Studies on the total synthesis of clavaserine. I. synthesis of 3-[3'R, 5'S]-7'-oxo-1'-aza-4'-oxa[3.2.0]hept-3'-yl]-3-O-benzyl-(2S, 3S)-serine and its (3'R, 5'R)-epimer from D-glucose

Acta Chimica Sinica ›› 1993, Vol. 51 ›› Issue (11): 1125-1132. Previous Articles Next Articles

Original Articles

棒丝氨酸的全合成研究I. 从D-葡萄糖合成3-[3'R, 5'S)-7'-氧代-1'-氮杂-4'-氧杂双环[3.2.0]-庚-3'-基]-3-O-苄基-(2S, 3S)-丝氨酸及其(3'R, 5'R)-差向异构体

张军良;张秋荣;甄济生;张致平

北京医科大学药学院有机化学教研室;中国医学科学院医药生物技术研究所

发布日期:1993-11-15

Studies on the total synthesis of clavaserine. I. synthesis of 3-[3'R, 5'S]-7'-oxo-1'-aza-4'-oxa[3.2.0]hept-3'-yl]-3-O-benzyl-(2S, 3S)-serine and its (3'R, 5'R)-epimer from D-glucose

ZHANG JUNLIANG;ZHANG QIURONG;ZHEN JISHENG;ZHANG ZHIPING

Published:1993-11-15

Abstract

The O-benzyl derivative of clavaserine 3-[(3'R,5'S)-7'-oxo-1'-aza-4'-oxabicyclo[3.2.0]hept-3'-yl]-3-O-benzyl-(2S ,3S)-serine (I) and its (3'R,5'R)-epimer were synthesized from D-glucose through reactions including the synthesis of side chain amino acid, the condensation with b-lactam, the formation of oxazolidine ring and the removal of protecting groups.

Key words: AMINO ACID, DERIVATIVES, GLUCOSE, LACTAM, ANTIBIOTICS

CLC Number:

R914

Cite this article

ZHANG JUNLIANG;ZHANG QIURONG;ZHEN JISHENG;ZHANG ZHIPING. Studies on the total synthesis of clavaserine. I. synthesis of 3-[3'R, 5'S]-7'-oxo-1'-aza-4'-oxa[3.2.0]hept-3'-yl]-3-O-benzyl-(2S, 3S)-serine and its (3'R, 5'R)-epimer from D-glucose[J]. Acta Chimica Sinica, 1993, 51(11): 1125-1132.

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棒丝氨酸的全合成研究I. 从D-葡萄糖合成3-[3'R, 5'S)-7'-氧代-1'-氮杂-4'-氧杂双环[3.2.0]-庚-3'-基]-3-O-苄基-(2S, 3S)-丝氨酸及其(3'R, 5'R)-差向异构体

Studies on the total synthesis of clavaserine. I. synthesis of 3-[3'R, 5'S]-7'-oxo-1'-aza-4'-oxa[3.2.0]hept-3'-yl]-3-O-benzyl-(2S, 3S)-serine and its (3'R, 5'R)-epimer from D-glucose

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