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Search for "desilylation" in Full Text gives 124 result(s) in Beilstein Journal of Organic Chemistry.

Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids

  • Ye Yuan,
  • Zhenhua Guan,
  • Xue-Jie Zhang,
  • Nanyu Yao,
  • Wenling Yuan,
  • Yonghui Zhang,
  • Ying Ye and
  • Zheng Xiang

Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111

Graphical Abstract
  • conditions, compound 15 and its diastereomer were obtained in a total yield of 90% at a ratio of 1:0.7. To improve the diastereoselectivity, we examined other reduction conditions and found that ʟ-Selectride afforded compound 15 in 90% yield with a dr of 9:1. Upon desilylation with TBAF, compound 15 was
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Published 21 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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Published 27 Jun 2025

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

Graphical Abstract
  • prepared via PMB removal of compound 21, which, in turn, was obtained through desulfonylation of compound 22. Compound 22 originated from the condensation of epoxide 23a with sulfone 26, which was produced by desilylation of 25 followed by converting the resulting primary alcohol into a sulfone group
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Published 12 Jun 2025

A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

  • Zhiyang Zhang,
  • Jialei Hu,
  • Hanfeng Ding,
  • Li Zhang and
  • Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

Graphical Abstract
  • oxidative cleavage [47] was applied to deliver aldehyde 29. Finally, a one-pot acetalization and desilylation effectively afforded the acetal alcohol, which was then oxidized with the aid of TPAP, furnishing acetal aldehyde 14 in 67% yield over two steps. With the two fragments 13 and 14 in hand, the next
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Published 12 May 2025

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

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  • oxidation then yields the intermediate. Subsequent desilylation and substrate/product exchange complete the catalytic cycle (Scheme 40). This approach underlines the potential of asymmetric electrosynthesis in achieving high selectivity and efficiency in complex molecule synthesis, further broadening the
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Published 09 Oct 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Graphical Abstract
  • Sonogashira cyclization sequence from (triisopropylsilyl)butadiyne (118). Subsequent immediate desilylation and Click reaction with organoazides lead to 4-pyrazolyl-1,2,3-triazoles 119 (Scheme 42) [139]. Notably, in some examples, it was even possible to synthesize the organoazides in situ from alkyl halides
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Published 16 Aug 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

Graphical Abstract
  • ) atom were well tolerated and the best result was obtained with a morpholine ring. Based on cyclic voltammetry studies, the transformation initiated with the anodic oxidation of hydrazone 101 to form highly electrophilic radical cationic species 104. Subsequent addition of azide 102 and desilylation
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Published 14 Aug 2024

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

  • Masahiro Terada,
  • Zen Iwasaki,
  • Ryohei Yazaki,
  • Shigenobu Umemiya and
  • Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

Graphical Abstract
  • , initiating further radical reactions through the formation of radical cations B. Nucleophilic arylmethyl radicals C, which are generated from radical cations B by desilylation, undergo an addition reaction with 2-benzopyrylium intermediates A, giving rise to the corresponding radical cation. Catalytic cycle
  • improved the yield of 3t (78%), presumably because of the retardation of the desilylation process (from B to C in Scheme 1a). Conclusion We have demonstrated a flow reaction system for a π-Lewis acidic metal-catalyzed cyclization/photochemical radical addition sequence, affording, in most cases, the 1H
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Published 13 Aug 2024

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

  • Senze Qiao,
  • Zhongyu Cheng and
  • Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

Graphical Abstract
  • then transformed into aldehyde 31 through several protecting group adjustments and the corresponding alcohol and Ley oxidation. After the preparation of 33 using Evans syn-aldol condensation as a critical step, 34 was produced by thioester formation, desilylation, and allylic oxidation. Incubating 34
  • and phosphonate 48, were synthesized, employing Evans’ vinylogous aldol and Myers’ auxiliary-mediated alkylation reactions as key steps. By utilizing these two fragments, a Horner–Wadsworth–Emmons olefination, followed by thioester formation and desilylation, produced several different activated
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Published 04 Apr 2024

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

  • Christina Schøttler,
  • Kasper Lund-Rasmussen,
  • Line Broløs,
  • Philip Vinterberg,
  • Ema Bazikova,
  • Viktor B. R. Pedersen and
  • Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

Graphical Abstract
  • , ethynylbenzene, or 4-ethynylbenzonitrile yielded compounds 19–21, while two-fold Sonogashira coupling with ((2-ethynylphenyl)ethynyl)triisopropylsilane resulted in compound 22. Desilylation of the alkynes of compound 22 with tetrabutylammonium fluoride (TBAF) and subsequent intramolecular Glaser–Hay coupling of
  • Sonogashira couplings of compound 25 with triisopropylsilylacetylene and ((2-ethynylphenyl)ethynyl)triisopropylsilane yielded compounds 26 and 27, respectively. A two-fold, intramolecular Glaser–Hay coupling of compound 27 (after desilylation) was attempted under the conditions that were successful in the
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Published 15 Jan 2024

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

  • Karolis Leitonas,
  • Brigita Vigante,
  • Dmytro Volyniuk,
  • Audrius Bucinskas,
  • Pavels Dimitrijevs,
  • Sindija Lapcinska,
  • Pavel Arsenyan and
  • Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

Graphical Abstract
  • copper(I) iodide in DMF/DIPEA solution at 55 °C with subsequent desilylation with potassium carbonate. Finally, butadiyne 6 was prepared by a homocoupling reaction of 5 with 80% yield. Derivatives containing two dicyanopyridyl moieties, 7 and 8, were prepared starting with a Sonogashira coupling of
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Published 12 Dec 2023

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

  • Feng Chen,
  • Xiu-Hua Xu,
  • Zeng-Hao Chen,
  • Yue Chen and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

Graphical Abstract
  • the synthesis of trifluoromethyl aromatic acyloins. Maekawa’s group [24] developed a tandem reaction of the reductive coupling between arylaldehydes and ethyl trifluoroacetate in the presence of magnesium and chlorotrimethylsilane, followed by desilylation to produce the trifluoromethyl aromatic
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Published 11 Sep 2023

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Graphical Abstract
  • whereas heating it in 75% acetic acid solution produced the deprotected compound but migration of the acyl group from the sn-2 to the sn-3 position lead to an inseparable mixture of regioisomers. A selective desilylation of 12.5 was finally achieved with BF3·Et2O producing 12.6 without migration of the
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Published 08 Sep 2023

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

  • Semyon V. Tsybulin,
  • Ekaterina A. Filatova,
  • Alexander F. Pozharskii,
  • Valery A. Ozeryanskii and
  • Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

Graphical Abstract
  • 10a–e on Al2O3 resulted in their quantitative desilylation with the formation of the target monomers 6a–e, thus eliminating the need to remove the trimethylsilyl protection. Pure samples of compounds 10a–e could be obtained by extraction of the reaction mixture with hexane followed by
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Published 15 May 2023

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

Graphical Abstract
  • [4][5][6][7][8][9][10], the RCM reaction constitutes a powerful tool to construct rings of various sizes. In 2009, Vanderwal and Dowling extended this process to the use of allylsilane derivatives which can be further submitted to an electrophilic desilylation reaction [51][52][53][54] giving an
  • electrophilic desilylation agents which can be used, a large diversity of compounds can be accessible through this method [51][52]. Oxidation followed by desilylation with fluoride source produces the natural product poitediol (118) in overall good yield. 2 Nozaki–Hiyama–Kishi (NHK) cyclization The Nozaki
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Published 03 Mar 2023

Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

  • Bilge Banu Yagci,
  • Selin Ezgi Donmez,
  • Onur Şahin and
  • Yunus Emre Türkmen

Beilstein J. Org. Chem. 2023, 19, 66–77, doi:10.3762/bjoc.19.6

Graphical Abstract
  • ) group via the β-silicon stabilization effect [36][37][38] as supported by computational studies [35]. The desilylation of intermediate 9 with the chloride of another molecule of 8 would result in the formation of final aza-Nazarov product 7 along with TMSCl (Scheme 1d). Five-membered nitrogen
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Published 17 Jan 2023

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

Graphical Abstract
  • cleavage [16] or from 1 by selective protection of the primary OH groups with tert-butyldimethylsilyl groups, followed by benzylation and desilylation [17][18]. We used both methods to prepare 6: The acetolysis method is convenient when perbenzyl α-cyclodextrin (2) is at hand but requires very strict
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Published 17 Nov 2022

Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

  • Anaïs Rousseau,
  • Guillaume Vincent and
  • Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

Graphical Abstract
  • coupling revealed the incompatibility of the lactone function; therefore, it was reduced with DIBAL-H then transformed into 19 by a one pot acetalization–desilylation procedure (91:9 mixture of diastereomers) [17]. Hydrozirconation followed by treatment with iodine furnished the target vinyl iodide 20
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Published 04 Oct 2022

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

  • Naoki Kise and
  • Toshihiko Sakurai

Beilstein J. Org. Chem. 2022, 18, 956–962, doi:10.3762/bjoc.18.95

Graphical Abstract
  • intramolecular addition of the anion D and subsequent O-trimethylsilylation of the resultant E produces intermediate 6 (path c). Desilylation of 6 with 1 M HCl and following dehydration of 7 affords product 3. On the other hand, O-trimethylsilylation of anion D forms N-(trimethylsilyl)ethenimine F and subsequent
  • treatment with 1 M HCl produces phthalide 4 through desilylation and following lactonization of F (path d). As can be seen from Scheme 5, the cyclization of D to E is the key step for the formation of compound 6. Therefore, we calculated the intermediates (D and E) and transition states (D–E TS) for this
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Published 02 Aug 2022

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • could have been due to an in situ chelation process. The level of selectivity was determined by HPLC to be >300:1 in favor of the β-configured cis-isomers (racemic mixture of 80a and 80b) [30]. Further, the desilylation using tetrabutylammonium fluoride (TBAF) gave racemic (±)-BCH-189 (1c). Chu et al
  • the α-anomer were produced individually by further deacetylation using methanolic ammonia and desilylation with TBAF [33]. (+)-BCH-189 (1a) was found to be less active against HIV-1 (EC50 = 0.2 µM in CEM cells) than (−)-BCH-189 (1, EC50 = 0.07 µM in CEM cells) [14]. Chu and co-workers [44] reported a
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Published 04 Nov 2021

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

  • Mathias B. Danielsen and
  • Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

Graphical Abstract
  • to create an epimeric mixture of the dinucleotide phosphoramidate-linked derivatives with subsequent separation of the two stereoisomers. These were then incorporated into the desired ONs after O3’-desilylation and phosphitylation of the dimers [107]. The authors found that for each of the sequences
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Published 29 Jul 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Graphical Abstract
  • -isobutyrylguanine, N-benzoylcytosine, 6-O-allylhypoxanthine or N,N-dibenzoyldiaminopurine in 53 to 83% yield. The desilylation of the nucleosides 3a–f with tetrabutylammonium fluoride in tetrahydrofuran (THF) led to the formation of six different double-headed nucleosides 4a–f (Scheme 1) [38][39]. The synthesized
  • nucleoside 102 with N1-benzoyl-5-ethynyluracil followed by desilylation produced the double-headed nucleoside 104, whereas the reaction of the azido nucleoside 102 with trimethylsilylacetylene (TMS-acetylene) followed by desilylation produced the nucleoside 105 (Scheme 23) [14]. Christensen et al. [31
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Published 08 Jun 2021

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

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Published 12 May 2021

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

  • Takashi Nishiyama,
  • Erina Hamada,
  • Daishi Ishii,
  • Yuuto Kihara,
  • Nanase Choshi,
  • Natsumi Nakanishi,
  • Mari Murakami,
  • Kimiko Taninaka,
  • Noriyuki Hatae and
  • Tominari Choshi

Beilstein J. Org. Chem. 2021, 17, 730–736, doi:10.3762/bjoc.17.62

Graphical Abstract
  • and desilylation, the electrocyclization of 29a proceeded smoothly to afford the desired 4-aminopyrroloquinoline 30a in 68% yield. Subsequently, the cycloamination of 30a in the presence of Pd(OAc)2, Cu(OAc)2, and K2CO3 gave tetrahydroquinoline 31 in 25% yield. However, although attempts were made to
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Published 16 Mar 2021

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

  • Mikhail K. Klychnikov,
  • Radek Pohl,
  • Ivana Císařová and
  • Ullrich Jahn

Beilstein J. Org. Chem. 2021, 17, 688–704, doi:10.3762/bjoc.17.58

Graphical Abstract
  • oxide ((R)-7b) provided the product (2S,4R)-9i in a much better 8:1 anti/syn coupling diastereoselectivity (Table 2, entry 10). The configuration of the major anti-diastereomer of alkoxyamine 9j was determined by X-ray crystallography after desilylation and hydrochloride formation (see Supporting
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Published 09 Mar 2021
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