FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE

DOI: 10.1016/S0040-4039(00)88685-2

Source and publish data:

Tetrahedron Letters p. 4021 - 4024 (1982)

Update date:2022-08-03

Topics: Synthesis Yield Purification Reaction Conditions Carbapenem Penicillin

Authors:

Hirai, Koichi

Iwano, Yuji

Fujimoto, Katsumi

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4039(00)88685-2

6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.

Full text of DOI:10.1016/S0040-4039(00)88685-2

Products guided by the article

Product name:(2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Cas No:92008-62-3

R&D Labs maybe for 92008-62-3

Ningbo Distant Chemicals Co.,Ltd

Contact:86-574-27862490,27862438

Address:5F-3,#54 DaShaNi street,Ningbo,CHINA
Jiangxi Hessence Chemicals Co., Ltd.

Contact:+86 796 3511924

Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
Nanjing Spring & Autumn Biological Engineering Co., Ltd.

Contact:86-180510-83338

Address:Suite# 210, No. 1 BuildingNanjing Agricultural Biotechnology High-tech Entrepreneurship Center, No. 4 Tongwei Road, Xuanwu District, Nanjing,China
Chengdu Chengnuo New-Tech Co., Ltd

Contact:0086-028-85749078

Address:4 Jiuyang road,Jiulong industrial port,Chengdu, China
Henan Surface Industry Co Ltd

Contact:86-371-86169316

Address:No.1,Shakou Road,Zhengzhou,China

Relevant to this article

Doi:10.1039/jr9630001982
(1963)
Doi:10.1007/BF00847799
()
Ring closing metathesis of α- and β-amino acid derived dienes

Doi:10.1016/j.jorganchem.2006.09.061
(2006)
Novel syntheses of chiral β- and γ-amino acid derivatives utilizing N-protected (aminoacyl)benzotriazoles from aspartic and glutamic acids

Doi:10.1021/jo061667s
(2007)
Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase

Doi:10.1016/j.bmcl.2016.04.031
(2016)
Hypervalent Iodine Oxidation of N-Acylhydrazones and N-Phenylsemicarbazone: An Efficient Method for the Synthesis of Derivatives of 1,3,4-Oxadiazoles and Δ³-1,3,4-Oxadiazolines

Doi:10.1021/jo00064a027
(1993)

Article Doi