sporaricin类似物、2-脱氧-4-N-甘氨酰基-6-O-(α-新壳二糖胺基)福他胺及其3-去氧甲基化合物的合成

Syntheses of sporaricin analogues, 2-deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine and its 3-de-O-methyl compound.

作者信息

Yamaguchi T, Kyotani Y, Watanabe I, Sato S, Takahashi Y, Nagakura M, Mori T

出版信息

J Antibiot (Tokyo). 1979 Nov;32(11):1137-46. doi: 10.7164/antibiotics.32.1137.

DOI:10.7164/antibiotics.32.1137

Abstract

2-Deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine (21) and 3-de-O-methyl-2-deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine (27) were prepared starting from lividamine. The syntheses include four key steps, that is, transformation of 2-deoxystreptamine moiety of lividamine to 4-N,3-O-didemethyl-2-deoxyfortamine, selective 4-N-methylation of the new aminocyclitol moiety, selective attachment of a glycyl residue to the methylamino group at C-4 and selective amination at C-6'.

摘要

以青紫胺为起始原料制备了2-脱氧-4-N-甘氨酰基-6-O-(α-氨基葡萄糖基)福他霉素(21)和3-O-去甲基-2-脱氧-4-N-甘氨酰基-6-O-(α-氨基葡萄糖基)福他霉素(27)。合成过程包括四个关键步骤，即青紫胺的2-脱氧链霉胺部分转化为4-N,3-O-二去甲基-2-脱氧福他霉素，新氨基环醇部分的选择性4-N-甲基化，甘氨酰基残基选择性连接到C-4位的甲氨基上以及C-6'位的选择性胺化。