REDOX GLYCOSIDATION - STEREOSELECTIVE SYNTHESES OF 1 -] 6 LINKED DISACCHARIDES VIA THIONOESTER INTERMEDIATES

被引：25

作者：

BARRETT, AGM

LEE, AC

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 10期

关键词：

D O I：

10.1021/jo00036a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.

引用

页码：2818 / 2824

页数：7

共 26 条

[1] PHOTOCHEMICAL TRANSFORMATIONS .30. PHOTOLYSIS OF THIOBENZOIC ACID O-ESTERS .1. PHOTOLYSIS OF O-CHOLESTERYL THIOBENZOATE
ACHMATOWICZ, S
BARTON, DHR
MAGNUS, PD
POULTON, GA
WEST, PJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (15): : 1567 - 1570
[2] REDOX GLYCOSIDATION - A STEREOSELECTIVE SYNTHESIS OF SUCROSE
BARRETT, AGM
BEZUIDENHOUDT, BCB
MELCHER, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) : 5196 - 5197
[3] BARRETT AGM, 1989, HETEROCYCLES, V28, P209
[4] REDOX GLYCOSIDATION - A NEW STRATEGY FOR DISACCHARIDE SYNTHESIS
BARRETT, AGM
BEZUIDENHOUDT, BCB
GASIECKI, AF
HOWELL, AR
RUSSELL, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) : 1392 - 1396
[5] REDOX GLYCOSIDATION VIA THIONOESTER INTERMEDIATES
BARRETT, AGM
BEZUIDENHOUDT, BCB
HOWELL, AR
LEE, AC
RUSSELL, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) : 2275 - 2277
[6] BARRETT AGM, UNPUB
[7] Bush CA, 1988, B MAGN RESON, V10, P73
[8] DESULFURIZATION OF THIOESTERS
ELLIS, J
SCHIBECI, RA
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (02) : 429 - 433
[9] ALLYL ETHER AS A PROTECTING GROUP IN CARBOHYDRATE CHEMISTRY .5. PREPARATION OF BENZYL ETHERS OF CARBOHYDRATES FOR USE IN OLIGOSACCHARIDE SYNTHESIS
GENT, PA
GIGG, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (12): : 1446 - 1455
[10] SYNTHESIS OF AND NUCLEAR-MAGNETIC-RESONANCE AND CONFORMATIONAL STUDIES ON SOME 1,2-LINKED DISACCHARIDE METHYL GLYCOSIDES CONTAINING D-MANNOSE AND L-RHAMNOSE
JANSSON, PE
KENNE, L
OTTOSSON, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (07): : 2011 - 2018

← 1 2 3 →