SYNTHESIS OF A CYCLOHEPTAOSE CONSISTING OF (1 -] 4)-LINKED 7-AMINO-6,7-DIDEOXY-ALPHA-D-GLUCO-HEPTOPYRANOSYL UNITS - A NEW ANALOG OF CYCLOMALTOHEPTAOSE

被引：26

作者：

BAER, HH ^{[1
]}

SHEN, YP ^{[1
]}

GONZALEZ, FS ^{[1
]}

BERENGUEL, AV ^{[1
]}

GARCIA, JI ^{[1
]}

机构：

[1] UNIV GRANADA,FAC CIENCIAS,DEPT QUIM ORGAN,E-18071 GRANADA,SPAIN

来源：

CARBOHYDRATE RESEARCH | 1992年 / 235卷

关键词：

D O I：

10.1016/0008-6215(92)80083-D

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Approaches to chain extension al the C-6 positions in cyclomaltoheptaose (1) were examined with the aim of producing novel beta-cyclodextrin analogs composed of heptose or hepturonic acid units. Iron carbonyl-mediated methoxycarbonylation, and nucleophilic displacement by cyanide, in the fully acetylated heptakis(6-deoxy-6-iodo) and heptakis(6-O-mesyl) derivates of 1, respectively, were unsuccessful, as were similar reactions attempted with the newly synthesized, analogous allyl-protected derivatives of 1. However, reaction of unprotected heptakis(6-deoxy-6-iodo)cyclomaltoheptaose with lithium cyanide in N,N-dimethylformamide afforded a high yield of the corresponding heptakis(6-cyano-6-deoxy) compound, namely, cyclohepta-(1 --> 4)-(6-deoxy-alpha-D-gluco-heptopyranosid)urononitrile, catalytic hydrogenation of which gave the title compound, cyclo-(1 --> 4)-(7-amino-6,7-dideoxy-alpha-D-glucoheptopyrano)heptaose, isolated as its peracetyl derivative.

引用

页码：129 / 139

页数：11

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