New synthetic route of guanidine from trichloroacetamide for tetrodotoxin and its related compounds.

被引：31

作者：

Nishikawa, T ^{[1
]}

Ohyabu, N ^{[1
]}

Yamamoto, N ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 14期

关键词：

guanidine; protecting group; hydrogenolysis; toxins;

D O I：

10.1016/S0040-4020(99)00140-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trichloroacetamide was transformed into dibenzylguanidinium salt in three steps. Attempted debenzylation was very difficult in the guanidinium form even under high pressure hydrogen and high temperature conditions. On the other hand, the benzyl groups on acetylated guanidine were easily deprotected by hydrogenolysis under 1 arm of hydrogen. These methods were applied to the syntheses of tetrodotoxin-related compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4325 / 4340

页数：16

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