SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .3. A SYNTHESIS OF A KEY INTERMEDIATE FOR 1-BETA-METHYLCARBAPENEM

被引：0

作者：

SASAKI, A ^{[1
]}

MATSUMURA, H ^{[1
]}

YANO, T ^{[1
]}

TAKATA, S ^{[1
]}

SUNAGAWA, M ^{[1
]}

机构：

[1] SUMITOMO PHARMACEUT CO LTD, RES LABS, 3-1-98 KASUGADE NAKA, KONOHANA KU, OSAKA 554, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 05期

关键词：

1-ALPHA-METHYLCARBAPENEM; 1-BETA-METHYLCARBAPENEM; (3S; 4S)-4-[(R)-1-CARBOXYETHYL]-3-[(R)-1-HYDROXYETHYL]-2-AZETIDINONE; STEREOSELECTIVE HYDROGENATION; STEREOSELECTIVE HYDROBORATION;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We synthesized useful intermediates 5 and 6 for 1-beta- and 1-alpha-methylcarbapenems from 4-carboxy-3-[(R)-1-hydroxyethyl]-2-azetidinone 4 as a starting material by using stereoselective hydrogenation and hydroboration, respectively. A practical synthetic route from 4 to the (3S,4S)4-[(R)-1-carboxyethyl]-3-[(R)-1-hydroxyethyl]-2-azetidinone derivative 1, a useful intermediate for the synthesis of 1-beta-methylcarbapenem antibiotics, was established.

引用

页码：1098 / 1104

页数：7

共 50 条

[21] A HIGHLY STEREOSELECTIVE SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE FROM (R)-3-HYDROXYBUTYRIC ACID
KOBAYASHI, Y
ITO, Y
TERASHIMA, S
TETRAHEDRON, 1992, 48 (01) : 55 - 66
[22] AN ENANTIOSELECTIVE SYNTHESIS OF THE KEY INTERMEDIATE FOR THE PREPARATION OF 1BETA-METHYLCARBAPENEM ANTIBIOTICS
HONDA, T
ISHIZONE, H
NAITO, K
SUZUKI, Y
HETEROCYCLES, 1990, 31 (07) : 1225 - 1228
[23] A SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE BY DEALLYLOXYCARBONYLATION USING PALLADIUM COMPLEXES
MURAYAMA, T
YOSHIDA, A
KOBAYASHI, T
MIURA, T
TETRAHEDRON LETTERS, 1994, 35 (15) : 2271 - 2274
[24] Stereoselective Synthesis of 4-Acetoxyazetidione: the Key Intermediate of Penem and Carbapenem Antibiotics
Xu, Xiaobo
Yang, Yingbin
Deng, Qin
Xiang, Li
Xiang, Jiannan
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (07) : 1017 - 1020
[25] SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .1. FACILE SYNTHESIS OF A KEY INTERMEDIATE - 4-ACETOXY-3-(1-HYDROXYETHYL)-2-AZETIDINONE
SUNAGAWA, M
MATSUMURA, H
ENOMOTO, M
INOUE, T
SASAKI, A
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (08) : 1931 - 1938
[26] SIMPLE, STEREOCONTROLLED SYNTHESIS OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM 3(R)-HYDROXYBUTYRIC ACID
IIMORI, T
SHIBASAKI, M
TETRAHEDRON LETTERS, 1986, 27 (19) : 2149 - 2152
[27] SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE INVOLVING DIVALENT TIN ENOLATES
DEZIEL, R
FAVREAU, D
TETRAHEDRON LETTERS, 1986, 27 (47) : 5687 - 5690
[28] A NEW SYNTHETIC ROUTE TO THE KEY PRECURSOR OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPANOATE
SHIRAI, F
NAKAI, T
CHEMISTRY LETTERS, 1989, (03) : 445 - 448
[29] Synthesis of the 1 beta-methylcarbapenem key intermediate
Goo, YM
Seo, MH
Lee, YY
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1997, 18 (09) : 1032 - 1034
[30] A NOVEL AND EFFICIENT SYNTHESIS OF THE KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS EMPLOYING [2+2]-CYCLOADDITION REACTION OF DIKETENE WITH A CHIRAL IMINE
KAWABATA, T
KIMURA, Y
ITO, Y
TERASHIMA, S
SASAKI, A
SUNAGAWA, M
TETRAHEDRON, 1988, 44 (08) : 2149 - 2165

← 1 2 3 4 5 →