Amino acid based diastereoselective synthesis of fucosamines
Amino acid based diastereoselective synthesis of fucosamines
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DOI：
10.1016/s0957-4166(02)00376-2
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发表时间：
2002-08-01
影响因子：
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通讯作者：
Quintela, JM
中科院分区：
文献类型：
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作者：
Ruiz, M;Ojea, V;Quintela, JM
对映体纯的 (+)-D-岩藻糖胺 1、(+)-N-甲基-D-岩藻糖胺 2 和 (+)-3-O-甲基-D-岩藻糖胺 3（埃尔胺糖）是由源自天然氨基酸的已知结构单元合成的。关键中间体 8 的直接和非对映选择性构建是通过锂化 Scholkopf 双内酰亚胺醚 7 和 1,3-二氧戊环-4-甲醛 5 之间的高度顺式、反选择性羟醛反应来完成的。通用中间体的精制需要任选的甲基化、在异丙叉缩酮存在下双内酰亚胺醚的选择性水解、内酯化和羧基的部分还原。组。 (C) 2002 Elsevier Science Ltd. 保留所有权利。
Enantiomerically pure (+)-D-fucosamine 1, (+)-N-methyl-D-fucosamine 2 and (+)-3-O-methyl-D-fucosamine 3 (elsaminose) have been synthesised from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 8 was accomplished by a highly syn,anti-selective aldol reaction between lithiated Schollkopf's bis-lactim ether 7 and the 1,3-dioxolane-4-carboxaldehyde 5. Elaboration of the common intermediate required optional methylation, selective hydrolysis of the bis-lactim ether in the presence of an isopropylidene ketal, lactonization and partial reduction of the carboxylic group. (C) 2002 Elsevier Science Ltd. All rights reserved.