A novel synthesis of D-galactofuranosyl, D-glucofuranosyl and D-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors

被引：32

作者：

Ferrières, V ^{[1
]}

Blanchard, S ^{[1
]}

Fischer, D ^{[1
]}

Plusquellec, D ^{[1
]}

机构：

[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6052, Inst Chim Rennes, F-35700 Rennes, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 24期

关键词：

D O I：

10.1016/S0960-894X(02)00822-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3515 / 3518

页数：4

共 24 条

[1] HUDSONS RULES OF ISO-ROTATION AS APPLIED TO FURANOSIDES, AND THE CONFORMATIONS OF METHYL ALDOFURANOSIDES [J].

ANGYAL, SJ .

CARBOHYDRATE RESEARCH, 1979, 77 (DEC) :37-50

[2] Synthesis and liquid-crystalline properties of novel archaeal diether-type glycolipids possessing one or two furanosyl units [J].

Auzély-Velty, R ;

Benvegnu, T ;

Mackenzie, G ;

Haley, JA ;

Goodby, JW ;

Plusquellec, D .

CARBOHYDRATE RESEARCH, 1998, 314 (1-2) :65-77

[3] Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-D-galactose and UDP-(2-deoxy-2-fluoro)-D-galactose and substrate activity with UDP-galactopyranose mutase [J].

Barlow, JN ;

Blanchard, JS .

CARBOHYDRATE RESEARCH, 2000, 328 (04) :473-480

[4] Positional isotope exchange catalyzed by UDP-galactopyranose mutase [J].

Barlow, JN ;

Girvin, ME ;

Blanchard, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6968-6969

[5] THE ENVELOPE OF MYCOBACTERIA [J].

BRENNAN, PJ ;

NIKAIDO, H .

ANNUAL REVIEW OF BIOCHEMISTRY, 1995, 64 :29-63

[6] SYNTHESIS OF BETA-D-GALACTOFURANOSE 1-PHOSPHATE [J].

CHITTENDEN, GJ .

CARBOHYDRATE RESEARCH, 1972, 25 (01) :35-41

[7] SYNTHESIS OF ALPHA-D-GALACTOFURANOSYL PHOSPHATE [J].

DELEDERKREMER, RM ;

NAHMAD, VB ;

VARELA, O .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :690-692

[8] GALACTOFURANOSE-CONTAINING GLYCOCONJUGATES IN TRYPANOSOMATIDS [J].

DELEDERKREMER, RM ;

COLLI, W .

GLYCOBIOLOGY, 1995, 5 (06) :547-552

[9] A new approach to a disaccharidic hapten containing a galactofuranosyl entity [J].

Ferrières, V ;

Roussel, M ;

Gelin, M ;

Plusquellec, D .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2001, 20 (09) :855-865

[10] An efficient route to per-O-acetylated hexofuranoses [J].

Ferrières, V ;

Gelin, M ;

Boulch, R ;

Toupet, L ;

Plusquellec, D .

CARBOHYDRATE RESEARCH, 1998, 314 (1-2) :79-83

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