Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• were calculated using the Gaussian 03 program with DFT at the B3LYP/3-21G for C and H [33], and the LanL2DZ basis set and effective core potential (ECP) for La [29][32]. La@C2v-C82(CH2C6H4CH3) (2a): vis–NIR (CS2): λmax = 572, 741, 1304 nm; MALDI–TOF MS (m/z): [MH]+ calcd for LaC90H9, 1228.98; found

• , 1229.04. La@C2v-C82(CH2C6H4CH3) (3a): vis–NIR (CS2): λmax = 560, 851, 991, 1271 nm; MALDI–TOF MS (m/z): [MH]+ calcd for LaC90H9, 1228.98; found, 1228.99. La@C2v-C82(CH2C6H4CH3) (4a): vis–NIR (CS2): λmax = 525, 986, 1410 nm; MALDI–TOF MS (m/z): [MH]+ calcd for LaC90H9, 1228.98; found, 1229.15. La@C2v-C82

• (CH2C6H4CH3) (5a): vis–NIR (CS2): λmax = 809, 997, 1454 nm; MALDI–TOF MS (m/z): [MH]+ calcd for LaC90H9, 1228.98; found, 1229.04. La@C2v-C82(CH2C6H4CCSi(CH3)3) (2b): vis–NIR (CS2): λmax = 568, 762, 1307 nm; MALDI–TOF MS (m/z): [MH]+ calcd for LaC94H16Si, 1311.01; found, 1311.25. La@C2v-C82(CH2C6H4CCSi(CH3)3

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• MALDI-TOF-MS techniques. To examine the electronic properties of D–A TPECNz, density functional theory (DFT) calculations at the B3LYP level of theory with the 6-31G(d,p) basis set were performed. It has been previously reported that the twist angle of the D–A segment has a significant role in

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• ). Obtained data were processed with Win-GPC software. Matrix-assisted laser desorption/ionization time-of-flight mass spectra (MALDI-TOF MS) were recorded on an Autoflex II (Bruker Daltonics, Bremen, Germany) using an N2 laser (λ = 337 nm). All spectra were recorded in positive reflector mode. Detection was

• distributions (ε) and (δ) of low intensity can be attributed to a methyl-initiated and proton-initiated PEtOx formed after termination at position C2 with the final fragmentation of the formed ester group during the MALDI-TOF MS assay carrying Na+ and H+ ions, respectively. It is well known that water and

• obtained via a chain-transfer reaction containing an NHCH=CH2 end group with Na+ (δ). The Mn of the resulting polymers remains lower than expected from the [M]0/[I]0 ratio. As observed in MALDI-TOF MS, the primary molar mass distribution of the resulting polymer after BnBr initiation can be attributed to

A study of the DIBAL-promoted selective debenzylation of α-cyclodextrin protected with two different benzyl groups

• Naser-Abdul Yousefi,
• Morten L. Zimmermann and
• Mikael Bols

Beilstein J. Org. Chem. 2022, 18, 1553–1559, doi:10.3762/bjoc.18.165

• in Table 1. Firstly, reaction with DIBAL in toluene at 0.3 M concentration and at 50 °C gave after 24 h almost complete conversion of the starting material to a symmetrical compound 8 that according to MALDI–TOF MS has lost two DCB groups and not any benzyl group. The compound was analyzed with 1H

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

• Md Azadur Rahman,
• Kana Kuroda,
• Hirofumi Endo,
• Norihiko Sasaki,
• Tomoaki Hamada,
• Hiraku Sakai and
• Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

• obtained at T1 = −60 °C and T2 = −30 °C, although heptasaccharide 7a was not produced. MALDI–TOF MS spectra indicated the formation of byproducts derived from longer oligosaccharides at T1 = −30 °C and T2 = −30 °C (Figure 5). The relative intensity of the molecular ion peaks of hydroxy-substituted sugars

• (T2) on the yield of oligosaccharides. Influence of temperatures of anodic oxidation (T1) and glycosylation (T2). MALDI–TOF MS spectra of oligosaccharides. Proposed structures of byproducts of electrochemical polyglycosylation. Proposed mechanisms of electrochemical polyglycosylation. Oxidative

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• , 3H); 13C NMR (100 MHz, DMSO-d6, 25 °C) δ 168.55, 148.01, 143.23, 137.64, 126.25, 110.44, 62.71, 62.63, 62.26, 50.89, 27.58; MALDI-TOF MS (m/z) [M + H]+ calcd for C53H49N18O18, 1225.3467; found, 1225.3449 (Δ = −1.5 ppm). Synthesis of compound TBTQ-CB6. Compound 3 (0.27 g, 0.22 mmol) was dissolved in a

• solid (0.28 g, 97%). Mp 198.2–199.4 °C; 1H NMR (400 MHz, D2O, 25 °C) δ 7.89 (s, 6H), 7.21 (s, 6H), 5.25 (s, 12H), 4.97, 4.91 (ABq, J = 17.2 Hz, 12H), 4.31 (s, 3H), 1.57 (s, 3H); 13C NMR (100 MHz, D2O, 25 °C) δ 172.58, 147.37, 143.07, 138.51, 126.22, 110.74, 63.11, 62.15, 61.82, 52.77, 24.69; MALDI-TOF

• MS (m/z) [M – 6NH4 + 6H + Na]+ calcd for C53H48N18O18Na, 1247.3286; found, 1247.3211 (Δ = −6.0 ppm); [M – 6NH4 + 7H]+ calcd for C53H49N18O18, 1225.3467; found, 1225.3252 (Δ = −17.6 ppm), and [M – 6NH4 + 5H + 2 Na]+ calcd for C53H47N18Na2O18, 1269.3106; found, 1269.3199 (Δ = + 7.3 ppm). (a) 1H NMR

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• macrocyclisation product, which was confirmed by MALDI-ToF-MS of the crude reaction mixture after test cleavage (see Supporting Information File 1, Figure S1). However, deboronation and dehalogenation were observed as side reactions to some extent as well as oxidation, most likely of methionine (Met) [79]. The

Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

• Xinru Sheng,
• Errui Li and
• Feihe Huang

Beilstein J. Org. Chem. 2020, 16, 2954–2959, doi:10.3762/bjoc.16.245

• . Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI–TOF MS) was conducted to investigate the complexation properties. However, no signal related to the complex but only peaks of H were found, implying weak host–guest interactions between H and G (Figures S3 and S4

Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation

• Jennifer Frommer and
• Sabine Müller

Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234

• Supporting Information File 1). The presence of the modified ribonucleotide in the synthesized sequence was confirmed by MALDI–TOF MS (Figure S1, Supporting Information File 1). Conclusion Oligonucleotides carrying a specific modification or functional entity at a pre-defined position are in high demand for

• equiv TEA, DCM, room temperature, 1 h, 52%. Variation of reaction conditions for 2’-/3’-O silylation of adenosine derivative 7. Supporting Information Supporting Information File 434: Experimental procedures, RNA synthesis, characterization data (1H, 13C NMR, MALDI–TOF MS, PAGE), copies of 1H and 13C

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• –Ishiyama borylation step is possibly increased by further conditions screening. The thus-obtained 1 was identical to the product from the C–H borylation of HBC according to 1H NMR spectroscopy, and the 13C NMR and HRMS by MALDI–TOF MS results also supported the identification. The hexaborylated HBC 1 was

• JEOL JMS-S3000 SpiralTOF (MALDI–TOF MS). Nuclear magnetic resonance (NMR) spectra were recorded on a JEOL ECS-600 (1H 600 MHz, 13C 150 MHz) spectrometer or a JEOL ECA 600II spectrometer with UltraCoolTM probe (1H 600 MHz, 13C 150 MHz). Chemical shifts for 1H NMR are expressed in parts per million (ppm

• (1.1 mg, 0.8% yield based on 2) as an orange solid. 1H NMR (600 MHz, CDCl3) δ 9.78 (s, 1H), 1.61 (s, 6H); 13C NMR (150 MHz, CDCl3) δ 25.6, 84.4, 122.4, 127.0, 127.3, 128.8, 129.9; HRMS (MALDI–TOF MS) m/z: [M]+ calcd for C78H84B6O12, 1278.6571; found, 1278.6582. X-ray crystallography Details of the

Room-temperature Pd/Ag direct arylation enabled by a radical pathway

• Amy L. Mayhugh and
• Christine K. Luscombe

Beilstein J. Org. Chem. 2020, 16, 384–390, doi:10.3762/bjoc.16.36

• ring. Finally, branching is evidenced by the discrepancy in molecular weight as calculated for a linear polymer by 1H NMR compared with that indicated by MALDI–TOF MS (Figure 2). Due to the high regioselectivity in small molecule couplings, defects to this extent were unexpected. MALDI–TOF MS was

• Scheme 1. The region from 4–4.5 ppm indicates the interior indole repeat units compared with the terminal indole units. MALDI–TOF MS of PIn, indicating octylindole repeat units with three different types of end groups. These include 2-nitrophenyl, iodine, and hydrogen. A high yielding, highly selective

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

• Sabrina Müller,
• Jannik Paulus,
• Jochen Mattay,
• Heiko Ihmels,
• Veronica I. Dodero and
• Norbert Sewald

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

• in DMF for the synthesis of P2. However, in the case of P1 and P3, the formation of tetramethylguanidinium side products was detected by MALDI–TOF MS. This irreversible N-guanylation of the polyamide N-terminus resulted from slow carboxy activation of the building block by HBTU and the presence of an

• 2.5% TFA in dichloromethane. The free C-terminus of the polyamides was modified in solution with N,N-dimethylaminopropylamine by using PyBOP as an activating reagent to install the corresponding end group. The completeness of all reaction stages was checked by MALDI–TOF MS. Purification of the final

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• , even at increased reaction times. Minor products with more downfield chemical shifts were also observed via 1H NMR of these crude product mixtures; these were easily separated from quaterphenyl isomers using flash column chromatography. Analysis of the crude product mixtures by MALDI–TOF–MS confirmed

• through time-of-flight matrix assisted laser desorption ionization (MALDI–TOF–MS) mass spectrometry, using sulfur as a matrix. Suzuki–Miyaura coupling to form m,p’-quaterphenyl (13) [35]: 4-Biphenylboronic acid (0.18 g, 0.91 mmol) and 1 M K2CO3 (1.5 mL) were added to a 10 mL Pyrex microwave tube. 3

• the general rearrangement procedure. The crude product was purified via CombiFlash with hexanes to yield an off-white solid (7 mg, 70% yield) consisting of 13 (81%) and 14 (19%). Minor products were eluted with ethyl acetate. MALDI–TOF–MS analysis indicated oligomerization (m/z = 344, 673). o,m

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• ESI/APCI as an ion source and a manual pump for sampling. Matrix-assisted laser desorption ionization–time-of-flight mass spectra (MALDI–TOF MS) were measured on a MALDI–TOF MS UltrafleXtreme (Bruker Daltonics) and samples were ionized with the aid of a Nd:YAG laser (355 nm) from α-cyano-4

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

• Shahien Shahsavari,
• Dhananjani N. A. M. Eriyagama,
• Bhaskar Halami,
• Vagarshak Begoyan,
• Marina Tanasova,
• Jinsen Chen and
• Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

• (profile d). The purified de-tritylated ODN was further analyzed with polyacrylamide gel electrophoresis (PAGE), a single band was observed (Lane 1, Figure 5). The HPLC purified ODN was also analyzed with MALDI–TOF MS, molecular mass corresponding to correct ODN structure was found (Figure 6). The

• . The HPLC profiles of crude and pure 30c are given in Figure 4. Its PAGE and MALDI–TOF MS images are in Figure 5 and Figure 6, respectively. All analytical data for 30d,e are given in Supporting Information File 2. It is noted that aminolysis and hydrolysis of the sensitive groups in the ODNs, which

• ODN. The pure ODN was analyzed with PAGE and MALDI–TOF MS. Information about OD260 of the ODNs (30a–e) and a comparison of the synthesis yields of 30a using the dM-Dmoc (OD260 of 0.52 µmol synthesis, 2.94) and standard (OD260 of 0.52 µmol synthesis, 8.30) ODN synthesis technologies are provided in the

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• C545. Furthermore, E501 was substituted by phenylalanine to prevent coordination of the Glu side chain to the metal site and deactivation of the catalyst. Two specific TEV (Tobacco Etch Virus protease) cleavage sites were further introduced into loops 7 and 8 to facilitate MALDI–TOF–MS analysis. The

Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• spectrometry (MALDI–TOF MS, Figure 2). Several series of signals with a regular interval of 206.1 (repeating unit) were observed in the lower mass range. The m/z value of each signal of the major distribution corresponds with [166.0 (C6F5COO, initiating group) + 206.1n (repeating unit) + 59.1 (CH2CHMeOH

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• together with 5 mg/mL α-cyano-4-hydroxycinnamic acid (HCCA) matrix (70% ACN in 0.1% TFA solution in double distilled water). MALDI–TOF MS was performed on a AB 5800 MS (AB Sciex, Darmstadt, Germany) in positive ion mode. FimHtr FimHtr (3.36 nmol) was dissolved in PBS buffer (pH 7.8). Ligand 3 was dissolved

• ), 75.4 (1C, C-5), 72.4 (1C, C-3), 72.0 (1C, C-2), 60.3 (1C, C-4), 62.6 (1C, C-6), 43.8 (1C, CH2-ethyl), 42.1 (1C, CH2-ethyl) ppm; not visible owing to slow relaxation: 2 squaric acid C=O), CF3; 19F NMR (471 MHz, MeOH-d4) δ −66.84 (s) ppm; MALDI–TOF MS m/z: 620.72 [M]+. Nα-Boc-glycin-[p-(α-D

• ), 154.6 (1C, Caryl-4), 134.1 (1C, Caryl-1), 122.9 (2C, CHaryl-2,6), 118.1 (2C, CHaryl-3,5), 100.5 (1C, C-1), 80.7 (1C, C(CH3)3), 75.4 (1C, C-5), 72.4 (1C, C-3), 72.0 (1C, C-2), 68.4 (1C, C-4), 62.7 (1C, C-6), 45.0 (1C, CH2-glycine), 28.7 (3C, C(CH3)3) ppm; MALDI–TOF MS m/z: 451.10 [M + Na]+; ESIMS m/z

Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

• Bimal Koirala,
• Robert A. Hillman,
• Erin K. Tiwold,
• Michael A. Bertucci and
• Yftah Tal-Gan

Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

• desorption ionization time-of-flight mass spectrometry (MALDI–TOF MS) data were obtained on either a Bruker Autoflex or Bruker Microflex spectrometer equipped with a 60 Hz nitrogen laser and a reflectron. In positive ion mode, the acceleration voltage on Ion Source 1 was 19.01 kV. Exact mass (EM) data were

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• characterized by 1H NMR, 13C NMR and MALDI–TOF–MS analyses (see Supporting Information File 1). The catalytic performance of the synthesized imidazolium salts as NHC precursors for Pd-catalyzed Mizoroki–Heck reactions in water was investigated. A model reaction was carried out by using 4-bromoacetophenone (1a

• , NCH2), 3.66–3.42 (m, 196H, CH2 of PEG chain), 3.24 (s, 3H, PEG-OCH3); 13C NMR (CDCl3) δ 153.7, 149.6, 137.6, 137.3, 123.7, 123.0, 122.9, 122.7, 71.2–68.3 (CPEG), 58.1, 53.0, 49.0; MALDI–TOF–MS m/z: [Mn=49 − Br]+ calcd for C110H212N3O50, 2375.4; found, 2375.8. Imidazolium salt L2. Yield: 3.9 g (92

• , 128.7, 128.4, 123.1, 122.2, 71.34–68.2 (CPEG), 58.0, 51.7, 49.0; MALDI–TOF–MS m/z: [Mn=49 − Br]+ calcd for C111H213N2O50, 2374.4; found, 2374.8. Imidazolium salt L3. Yield: 3.8 g (88%), pale white solid; 1H NMR (DMSO-d6) δ 9.28 (s, 1H, CHimid), 8.15 (d, J = 8.0 Hz, 1H, CHAr), 8.04–8.03 (m, 2H, CHAr

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

• Julia Kinzel,
• Daniel F. Sauer,
• Marco Bocola,
• Marcus Arlt,
• Tayebeh Mirzaei Garakani,
• Andreas Thiel,
• Klaus Beckerle,
• Tino Polen,
• Jun Okuda and
• Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

• -d1 was dried over calcium hydride, distilled, degassed and stored in a glove box. NMR spectra were recorded on a Bruker DRX 400 spectrometer (1H, 400.1 MHz). Chemical shifts were referenced internally by using the residual solvent resonances [50]. MALDI–TOF MS spectra were recorded on an Ultraflex

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• structures of Sug-2 and Sug-3 have been characterized by 1H NMR, 13C NMR, and MALDI–TOF MS. The chemical structure of the obtained polymers was confirmed by 13C CP/MAS NMR and Fourier transform infrared spectroscopy (FTIR) (Figure S1, Supporting Information File 1). For example, the backbone and structure

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

• Jing Hu,
• Chris Weise,
• Christoph Böttcher,
• Hua Fan and
• Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

• , and tryptic peptides were analyzed either directly by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI–TOF MS) or guanidinated and then analyzed by MALDI. The labeled peptide peaks (Figure 2B) in the mass spectrum were identified as either GAT or GFP by matching the

• -day infection by flow cytometry and fluorescence microscopy to determine the cell surface expression of the GAT1/GFP fusion proteins. MALDI mass fingerprinting Using MALDI–TOF MS, protein fragments with blocked N-termini or that are available in limited concentrations can be easily analyzed. The MALDI

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

• Peter H. Seeberger,
• Claney L. Pereira and
• Subramanian Govindan

Beilstein J. Org. Chem. 2017, 13, 164–173, doi:10.3762/bjoc.13.19

• -dimethylformamide; EtOAc: ethyl acetate; GlcA: glucouronic acid; HPLC: high-performance liquid chromatography; Lev: levulinoyl; MALDI–TOF MS: matrix-assisted laser desorption/ionization–time of flight mass spectrometry; NAP: 2-naphthylmethyl; TBS: tert-butyldimethylsilyl; THF: tetrahydrofuran; TMSOTf

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• cyanotrihydroborate in dimethyl sulfoxide (DMSO) at 90 °C for 24 h. The product yield of multi-Lac-β-CD was 25%, and no unreacted compounds were confirmed by thin-layer chromatography (TLC). The MALDI–TOF MS spectrum of multi-Lac-β-CD revealed several peaks at m/z 2804, m/z 3006, m/z 3139, m/z 3296, and m/z 3454