A FACILE CONVERSION OF THE PHENYLTHIO GROUP TO ACETOXY BY COPPER REAGENTS FOR A PRACTICAL SYNTHESIS OF 4-ACETOXYAZETIDIN-2-ONE DERIVATIVES FROM (R)-BUTANE-1,3-DIOL

被引：52

作者：

NAKATSUKA, T ^{[1
]}

IWATA, H ^{[1
]}

TANAKA, R ^{[1
]}

IMAJO, S ^{[1
]}

ISHIGURO, M ^{[1
]}

机构：

[1] SUNTORY INST BIOMED RES,SHIMAMOTO,OSAKA 618,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 09期

关键词：

D O I：

10.1039/c39910000662

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(3S,4R,1'R)-4-Acetoxy-3-(1'-tert-butyldimethylsilyloxyethyl)-azetidin-2-one 8, an important intermediate for the synthesis of penem and carbapenem antibiotics, was synthesized from (R)-butane-1,3-diol 1, using chlorosulphonyl isocyanate for the formation of beta-lactam ring in which a significant solvent effect on the ratio of diastereoisomers 6a and 6b was observed; copper(II) acetate rather than the poisonous mercury(II) acetate was used to convert the phenylthio group of compound 6a to acetoxy.

引用

页码：662 / 664

页数：3

共 19 条

[11] A NOVEL SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE EMPLOYING THE [2+2]-CYCLOADDITION REACTION OF CHLOROSULFONYL ISOCYANATE WITH A 4H-1,3-DIOXIN DERIVATIVE
ITO, Y
KOBAYASHI, Y
TERASHIMA, S
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5631 - 5634
[12] A NOVEL SYNTHESIS OF (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE, THE VERSATILE KEY INTERMEDIATE OF CARBAPENEM SYNTHESIS, FROM (S)-ETHYL LACTATE
ITO, Y
KAWABATA, T
TERASHIMA, S
[J]. TETRAHEDRON LETTERS, 1986, 27 (47) : 5751 - 5754
[13] CONVENIENT METHOD FOR HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES USING CUPRIC CHLORIDE
NARASAKA, K
SAKASHIT.T
MUKAIYAM.T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (12) : 3724 - 3724
[14] OHASHI T, 1986, Patent No. 18791
[15] A STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN
SALZMANN, TN
RATCLIFFE, RW
CHRISTENSEN, BG
BOUFFARD, FA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (19) : 6161 - 6163
[16] SCHMID G, 1986, Patent No. 179318
[17] A SIMPLE PREPARATION OF (+)-4-PHENYLTHIOAZETIDIN-2-ONE AND AN ASYMMETRIC-SYNTHESIS OF (+)-THIENAMYCIN
SHIBASAKI, M
NISHIDA, A
IKEGAMI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (22) : 1324 - 1325
[18] STEREOCONTROLLED SYNTHESES OF CHIRAL INTERMEDIATES OF THIENAMYCIN FROM THREONINES
SHIOZAKI, M
ISHIDA, N
HIRAOKA, T
YANAGISAWA, H
[J]. TETRAHEDRON LETTERS, 1981, 22 (51) : 5205 - 5208
[19] YOSHIDA A, 1981, CHEM PHARM BULL, V29, P2899

← 1 2 →