Efficient total synthesis of the natural products 2,3,4,6-tetra-O-galloyl-d-glucopyranose, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose and the unnatural 1,2,3,4,6-penta-O-galloyl-alpha-D-glucopyranose

被引：38

作者：

Khanbabaee, K

Lotzerich, K

机构：

[1] Universität-GH-Paderborn, Fachbereich 13 - Organische Chemie, D-33098 Paderborn

来源：

TETRAHEDRON | 1997年 / 53卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(97)00702-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of the natural products 2,3,4,6-tetra-O-galloyl-D-glucopyranose (8). 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (10) and the unnatural 1,2,3,4,6-penta-O-galloyl-alpha-D-glucopyranose (13) was achieved based on a efficient esterification reaction of the benzylated galiic acid 5 with the alpha,beta-glucopyranoses 11 and 4, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：10725 / 10732

页数：8

共 25 条

[1] ARMITAGE R, 1961, LIEBIGS ANN CHEM, P1842
[2] BELL DJ, 1940, J CHEM SOC, V53, P453
[3] SIMPLE SYNTHESIS OF BETA-D-GLUCOSYL ESTERS
BOLS, M
HANSEN, HC
[J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (08): : 818 - 822
[4] GALLOTANNINS .13. STRUCTURE OF CHINESE GALLOTANNIN - EVIDENCE FOR A POLYGALLOYL CHAIN
BRITTON, G
CRABTREE, PW
HASLAM, E
STANGROO.JE
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (08): : 783 - &
[5] Ellagitannin chemistry. The first total chemical synthesis of an O(2),O(3)-galloyl-coupled ellagitannin, sanguiin H-5
Feldman, KS
Sambandam, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) : 8171 - 8178
[6] THE METABOLISM OF GALLIC ACID AND HEXAHYDROXYDIPHENIC ACID IN PLANTS .2. ESTERS OF (S)-HEXAHYDROXYDIPHENIC ACID WITH D-GLUCOPYRANOSE (C-4(1))
GUPTA, RK
ALSHAFI, SMK
LAYDEN, K
HASLAM, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11): : 2525 - 2534
[7] THE METABOLISM OF GALLIC ACID AND HEXAHYDROXYDIPHENIC ACID IN PLANTS .1. INTRODUCTION - NATURALLY-OCCURRING GALLOYL ESTERS
HADDOCK, EA
GUPTA, RK
ALSHAFI, SMK
HASLAM, E
MAGNOLATO, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11): : 2515 - 2524
[8] Hu┬fle G., 1978, ANGEW CHEM, V90, P602
[9] IKOTA N, 1991, CHEM PHARM BULL, V39, P2201
[10] Synthesis of trideca-O-methyl-alpha-pedunculagin. Diastereo-favoritism studies on intramolecular ester-cyclization of axially chiral diphenic acids with carbohydrate core
Itoh, T
Chika, J
Shirakami, S
Ito, H
Yoshida, T
Kubo, Y
Uenishi, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3700 - 3705

← 1 2 3 →