Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• synthesis of a range of aminoethyl glycosides (1–9) of common mono- and disaccharides. Although some of the glycosylation reactions could be improved by using alternative glycosylation methods (such as trichloroacetimidates, thiols), these would require more steps with chromatographic purifications and less

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• Neuenheimer Feld 253, D-69120 Heidelberg, Germany 10.3762/bjoc.6.72 Abstract (Oligo)phenothiazinyl thioacetates, synthesized by a one-pot sequence, are electrochemically oxidizable and highly fluorescent. SAMs can be readily formed from thiols prepared by in situ deprotection of the thioacetates in the

• presence of a gold-coated silicon wafer. Monolayer formation is confirmed by ellipsometry and the results compared to those obtained by force field and DFT calculations. Keywords: cyclic voltammetry; ellipsometry; phenothiazines; SAM; thiols; Introduction Functional organic π-systems [1] are of great

• become a groundbreaking strategy in the development of molecular electronics [6]. In recent years, many investigations into SAMs of organic molecules on gold surfaces have been carried out [7]. Thiols, thiol esters, and disulfides can be easily chemisorbed on gold to form SAMs by exposure of well-defined

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• thiols underwent S-trifluoromethylation smoothly in the presence of 1.1 equiv of 37 to afford the corresponding products in 51–99% yields (Scheme 29) [33]. The reaction outperforms other methods for synthesis of the SCF3 motif and shows high functional-group tolerance, and has particular application for

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles

• Dingqiao Yang,
• Ping Hu,
• Yuhua Long,
• Yujuan Wu,
• Heping Zeng,
• Hui Wang and
• Xiongjun Zuo

Beilstein J. Org. Chem. 2009, 5, No. 53, doi:10.3762/bjoc.5.53

• -catalyzed asymmetric ring-opening of oxabenzonorbornadiene with a wide range of nucleophiles including thiols [10], phenols [11], organoboronic acids [12][13], dialkylzincs [14][15], carboxylates [16], sulfur nucleophiles [17], and various amines [18][19]. In addition to rhodium catalysts, other transition

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

• Gareth J. Rowlands and
• Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

• ]paracyclophane compounds; aryl sulfonylation and the related sulfenylation facilitates the synthesis of sulfonic acids, sulfonamides and protected thiols [24][25][26] whilst directed metallation has allowed the formation of various sulfides [27][28][29][30]. Very few methodologies allow the synthesis of simple

• chiral monosubstituted thiols such as [2.2]paracyclophane-4-thiol 2 (Figure 1); the first reported preparations of racemic 2 were the conversion of 4-hydroxy[2.2]paracyclophane to the desired compound via a Newman-Kwart reaction or the direct reaction of 4-lithio[2.2]paracyclophane with sulfur [17]. Use

• [2.2]paracyclophane thiols; the first is that resolution of the planar chirality is complicit in the addition of the sulfur moiety and does not require resolution of any precursors. Secondly, the sulfinyl moiety permits further functionalisation of the [2.2]paracyclophane skeleton [33]. It is the

Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro- 2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium- 5-aminides

• Shuki Araki,
• Satoshi Hirose,
• Yoshikazu Konishi,
• Masatoshi Nogura and
• Tsunehisa Hirashita

Beilstein J. Org. Chem. 2009, 5, No. 8, doi:10.3762/bjoc.5.8

• (Scheme 2). The reactions with other nucleophiles than amines such as alcohols and thiols did not give the corresponding oxa- and thiadiazole derivatives. Reaction mechanism The reaction mechanism for the formation of triazole 3 was investigated. First, the 5-(benzylamino)tetrazolium salt 4a was treated

Variations in product in reactions of naphthoquinone with primary amines

• Marjit W. Singh,
• Anirban Karmakar,
• Nilotpal Barooah and
• Jubaraj B. Baruah

Beilstein J. Org. Chem. 2007, 3, No. 10, doi:10.1186/1860-5397-3-10

• rings are perpendicular to each other. The C-S bond formation reaction can be extended to other thiols such as thiophenol and 4-methoxythiophenol, 4-bromothiophenol etc. with 1,4-naphthoquinone as well as 1,4-benzoquinone. The difference in the case of reaction of 1,4-benzoquinone with primary amine

Chiral trimethylsilylated C₂-symmetrical diamines as phosphorous derivatizing agents for the determination of the enantiomeric excess of chiral alcohols by ¹H NMR

• Anne-Sophie Chauvin and
• Alexandre Alexakis

Beilstein J. Org. Chem. 2006, 2, No. 6, doi:10.1186/1860-5397-2-6

• agents (CDAs) developed contain an amine or a C2 symmetric diamine moiety, and have conveniently been applied to the determination of the enantiomeric excess (ee) of various chiral alcohols, [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20], amines,[6][13][14][21][22] thiols[3][10][12][13

Synthesis of phosphorothioates using thiophosphate salts

• Babak Kaboudin and
• Fatemeh Farjadian

Beilstein J. Org. Chem. 2006, 2, No. 4, doi:10.1186/1860-5397-2-4

• phosphorchloridate with thiols [22][23][24][25][26] and (iii) redox-type reactions of phosphorus triesters with thiols in the presence of tellurium (IV) chloride. [27][28] However, all of these methods have problems, including drastic reaction conditions and also some severe side reactions. Surface-mediated solid