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

收藏

页码：10725 / 10732

页数：8

相关论文

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 [J].

BOLS, M ;

HANSEN, HC .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (08) :818-822

[4] GALLOTANNINS .13. STRUCTURE OF CHINESE GALLOTANNIN - EVIDENCE FOR A POLYGALLOYL CHAIN [J].

BRITTON, G ;

CRABTREE, PW ;

HASLAM, E ;

STANGROO.JE .

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 [J].

Feldman, KS ;

Sambandam, A .

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)) [J].

GUPTA, RK ;

ALSHAFI, SMK ;

LAYDEN, K ;

HASLAM, E .

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 [J].

HADDOCK, EA ;

GUPTA, RK ;

ALSHAFI, SMK ;

HASLAM, E ;

MAGNOLATO, D .

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 [J].

Itoh, T ;

Chika, J ;

Shirakami, S ;

Ito, H ;

Yoshida, T ;

Kubo, Y ;

Uenishi, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3700-3705