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-bicyclo [3.2.0] hept-3'-yl]-3-O-benzyl-(2S, 3S)-serine and Its (3'R, 5'R)-epimer from D-glucose

作　　者：张军良[1] 张秋荣[2] 甄济生[2] 张致平[2] 

机构地区：[1]北京医科大学药学院有机化学教研室,北京100083 [2]中国医学科学院医药生物技术研究所,北京100050

出　　处：《化学学报》1993年第11期1125-1132,共8页Acta Chimica Sinica

摘　　要：以D-葡萄糖为原料经侧链氨基酸合成,与β-内酰胺缩合,嗯唑烷环合和除保护基等反应合成了棒丝氨酸的O-苄基衍生物,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(17)及其(3′R,5′R)差向异构体(18)。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-benzy]-(2S, 3S)-serine(17) and its (3'R, 5'R)-epimer (18) were synthesized from D-glucose through reactions in cluding the synthesis of sidechain amino acid, the consendation with β-lactam, the formation of oxa zolidine ring and the removal of protecting groups.

关 键 词：棒丝氨酸 氧青霉烷 棒霉素 抗菌素 

分 类 号：TQ463.53[化学工程—制药化工]