Direct synthesis of β-D-xyl-(1→2)-β-D-man-(1→4)-α-D-Glc-OMe:: a trisaccharide component of the Hyriopsis schlegelii glycosphingolipid

被引：18

作者：

Crich, D ^{[1
]}

Dai, ZM ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(98)00124-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the target trisaccharide is described in which the key beta-mannosylation is achieved in high yield and selectivity through reaction of the sulfoxide 7 with acceptor 8, mediated with triflic anhydride. The beta-xylosylation was best conducted using tribenzoyl xylopyranosyl bromide and silver triflate. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1681 / 1684

页数：4

共 20 条

[1] SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY
BARRESI, F
HINDSGAUL, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9376 - 9377
[2] STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES
BOCK, K
PEDERSEN, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03): : 293 - 299
[3] Chemistry of 1-alkoxy-1-glycosyl radicals: Formation of beta-mannopyranosides by radical decarboxylation and decarbonylation of manno-heptulosonic acid glycoside derivatives
Crich, D
Hwang, JT
Yuan, HW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6189 - 6198
[4] Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of alpha- to beta-pyranosides and the fragmentation of anomeric radicals
Crich, D
Sun, SX
Brunckova, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 605 - 615
[5] Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation
Crich, D
Sun, SX
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) : 11217 - 11223
[6] Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method
Crich, D
Sun, SX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4506 - 4507
[7] Direct synthesis of beta-mannopyranosides by the sulfoxide method
Crich, D
Sun, SX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1198 - 1199
[8] 1,5-ANHYDRO-XYLITOL
FLETCHER, HG
HUDSON, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (04) : 921 - 924
[9] GAREGG PJ, 1982, CARBOHYD RES, V108, P97
[10] A fundamentally new, simple, stereospecific synthesis of oligosaccharides containing the beta-mannopyranosyl and beta-rhamnopyranosyl linkage
Hodosi, G
Kovac, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2335 - 2336

← 1 2 →