A high-yielding, one-pot preparation of unsymmetrical glycosyl disulfides using 1-chlorobenzotriazole as an in situ trapping/oxidizing agent

被引：26

作者：

Stellenboom, Nashia ^{[1
]}

Hunter, Roger ^{[1
]}

Caira, Mino R. ^{[1
]}

Szilagyi, Laszlo ^{[2
]}

机构：

[1] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa

[2] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 40期

基金：

新加坡国家研究基金会;

关键词：

Unsymmetrical disulfide synthesis; Diglycosyl disulfide; BtCl; Sugar thiols; SOLID-PHASE; SELECTIVE GLYCOSYLATION; CONFORMATIONAL-ANALYSIS; DERIVATIVES; PROTEINS; TETRATHIOMOLYBDATE; GLYCOSYLDISULFIDES; DISACCHARIDE; CHEMISTRY; REAGENTS;

D O I：

10.1016/j.tetlet.2010.07.176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high-yielding, one-pot methodology for preparing unsymmetrical glycosyl disulfides derived from sugar, alkyl/aryl or cysteine thiols is reported using 1-chlorobenzotriazole (BtCl) as the oxidant. The highlight of the method is the low temperature of coupling (-78 degrees C) as well as the in situ trapping of the sulfenyl intermediate, which ensures that no homodimer of (RSH)-S-1 ((RSSR1)-S-1) is formed. The coupling efficiency is independent of sugar type, thiol position in the sugar, sugar-protecting groups, and the various products serve to illustrate the rapid synthetic access to a number of model systems in glycobiology. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5309 / 5312

页数：4

共 43 条

[1] AKAGI M, 1961, CHEM PHARM BULL, V9, P360
[2] Synthesis of some 6-S-heterocyclic Derivatives of 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose
Alho, MAM
DAccorso, NB
Thiel, IME
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) : 1339 - 1343
[3] Glycosyldisulfides from dynamic combinatorial libraries as O-glycoside mimetics for plant and endogenous lectins:: Their reactivities in solid-phase and cell assays and conformational analysis by molecular dynamics simulations
Andre, Sabine
Pei, Zhichao
Siebert, Hans-Christian
Ramstrom, Olof
Gabius, Hans-Joachim
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (18) : 6314 - 6326
[4] Antithrombotic and anticancer effects of garlic-derived sulfur compounds: A review
Ariga, Toyohiko
Seki, Taiichiro
[J]. BIOFACTORS, 2006, 26 (02) : 93 - 103
[5] REACTIONS OF TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLSULFENYL BROMIDE
BELL, RH
HORTON, D
MILLER, MJ
[J]. CARBOHYDRATE RESEARCH, 1969, 9 (02) : 201 - &
[6] From disulfide- to thioether-linked glycoproteins
Bernardes, Goncalo J. L.
Grayson, Elizabeth J.
Thompson, Sam
Chalker, Justin M.
Errey, James C.
El Oualid, Farid
Claridge, Timothy D. W.
Davis, Benjamin G.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2244 - 2247
[7] The direct formation of glycosyl thiols from reducing sugars allows one-pot protein glycoconjugation
Bernardes, Goncalo J. L.
Gamblin, David P.
Davis, Benjamin G.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) : 4007 - 4011
[8] Allicin, the antibacterial principle of Allium sativum I Isolation, physical properties and antibacterial action
Cavallito, CJ
Bailey, JH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 : 1950 - 1951
[9] CERNY M, 1959, COLLECT CZECH CHEM C, V24, P64
[10] 2,3,4,6-TETRA-0-ACETYL-BETA-D-GALAKTOPYRANOSYLMERCAPTAN UND DESSEN ANWENDUNG ZUR SYNTHESE VON BETA-D-THIOGALAKTOSIDEN
CERNY, M
PACAK, J
STANEK, J
[J]. MONATSHEFTE FUR CHEMIE, 1963, 94 (01): : 290 - &

← 1 2 3 4 5 →