One-pot synthesis of per-O-acetylated thioglycosides from unprotected reducing sugars

被引：80

作者：

Agnihotri, G ^{[1
]}

Tiwari, P ^{[1
]}

Misra, AK ^{[1
]}

机构：

[1] Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India

来源：

CARBOHYDRATE RESEARCH | 2005年 / 340卷 / 07期

关键词：

acetylation; thioglycosides; one-pot; stoichiometric; unprotected sugars; BF3-OEt2;

D O I：

10.1016/j.carres.2005.02.027

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A sequential per-O-acetylation and thioglycosidation of unprotected reducing sugars using a stoichiometric quantity of acetic anhydride and alkyl- or arylthiols is reported. These reactions, which are catalyzed by BF3 center dot OEt2, together constitute an efficient one-pot method for the synthesis of acetylated thioglycosides. (c) 2005 Published by Elsevier Ltd.

引用

页码：1393 / 1396

页数：4

共 20 条

[1]

[Anonymous], [No title captured]

[2] SYNTHESIS OF REDUCING DISACCHARIDES BEARING A LIPOPHILIC CHAIN FOR THE CONJUGATION TO PROTEINS [J].

CABARET, D ;

KAZANDJAN, R ;

WAKSELMAN, M .

CARBOHYDRATE RESEARCH, 1986, 149 (02) :464-470

[3] Synthesis of a versatile tetrasaccharide of sialyl Le(X) and Le(X) antigens [J].

Chowdhury, US .

TETRAHEDRON, 1996, 52 (39) :12775-12782

[4]

Das S.K., 1996, CARBOHYD RES, V296, P1079

[5] SYNTHESIS OF ETHYL AND PHENYL 1-THIO-1,2-TRANS-D-GLYCOPYRANOSIDES FROM THE CORRESPONDING PER-O-ACETYLATED GLYCOPYRANOSES HAVING A 1,2-TRANS-CONFIGURATION USING ANHYDROUS FERRIC-CHLORIDE AS A PROMOTER [J].

DASGUPTA, F ;

GAREGG, PJ .

ACTA CHEMICA SCANDINAVICA, 1989, 43 (05) :471-475

[6] Transition metal-catalyzed syntheses of 'rod-like' thioglycoside dimers [J].

Gan, ZH ;

Roy, R .

TETRAHEDRON LETTERS, 2000, 41 (08) :1155-1158

[7]

Garegg PJ, 1997, ADV CARBOHYD CHEM BI, V52, P179, DOI 10.1016/S0065-2318(08)60091-8

[8] Reaction of 1,2-trans-glycosyl acetates with thiourea:: a new entry to 1-thiosugars [J].

Ibatullin, FM ;

Shabalin, KA ;

Jänis, JV ;

Shavva, AG .

TETRAHEDRON LETTERS, 2003, 44 (43) :7961-7964

[9] A HIGHLY CONVERGENT SYNTHESIS OF THE TETRAGALACTOSE MOIETY OF THE GLYCOSYL PHOSPHATIDYL-INOSITOL ANCHOR OF THE VARIANT SURFACE GLYCOPROTEIN OF TRYPANOSOMA-BRUCEI [J].

KHIAR, N ;

MARTINLOMAS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7017-7021

[10] Synthesis and biological activities of three sulfated sialyl Le(x) ganglioside analogues for clarifying the real carbohydrate ligand structure of L-selectin [J].

Komba, S ;

Ishida, H ;

Kiso, M ;

Hasegawa, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (11) :1833-1847

← 1 2 →