Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

DOI: 10.1248/cpb.42.1381

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1381 - 1387 (1994)

Update date:2022-09-26

Topics:

Authors:

Sunagawa

Sasaki Sasaki

Matsumura

Goda Goda

Tamoto Tamoto

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

Article abstract of DOI:10.1248/cpb.42.1381

An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.

Full text of DOI:10.1248/cpb.42.1381

NII-Electronic Library Service

Products guided by the article

Product name:(3S,4S)-4-<(1S)-1-benzyloxycarbonylethyl>1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone

Cas No:105370-87-4

R&D Labs maybe for 105370-87-4

Du-Hope International Group

website:http://www.np-chem.com

Contact:0086-25-52346877

Address:199, Jian Ye Road, Nanjing, China
ChangZhou Mascotchem. Co.,Ltd.

website:http://www.mascotchem.com

Contact:86-519-85010339

Address:B-802,XingBei Building,391#,Tongjiang Middle Road New District,Changzhou,JS,China
Shanghai Bojing Chemical Co., Ltd.

Contact:021-37122233

Address:6F Buildiing 11,No.388,Baifu Road,District Fengxian.Shanghai, China.
jiangsu hualin chemical co.,ltd.

Contact:86-25-87787402

Address:jaingsu,china
Nanjing Yuance Industry&Trade Co., Ltd.

website:http://www.njyuance.cn/

Contact:+86-25-85439097

Address:B1702, Aoti Bldg, No. 130, Aoti Avenue, Nanjing, China

Relevant to this article

Physical Organic Approach to Persistent, Cyclable, Low-Potential Electrolytes for Flow Battery Applications

Doi:10.1021/jacs.7b00147
(2017)
Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases

Doi:10.1016/j.tet.2009.07.021
(2009)
Supramolecular aggregates of azobenzene phospholipids and related compounds in bilayer assemblies and other microheterogeneous media: Structure, properties, and photoreactivity

Doi:10.1021/ja971291n
(1997)
Synthesis and reactivity of rhodium(III) pentamethylcyclopentadienyl complexes of N-B-PTA(BH₃): X-ray crystal structures of [Cp^*RhCl₂{N-B}-PTA(BH₃)] and [Cp^*Rh{N-B-PTA(BH₃)}(η²-CH₂ = CHPh)]

Doi:10.1016/j.jorganchem.2008.04.006
(2008)
Doi:10.1002/hlca.19430260138
(1943)
Doi:10.1021/ja00213a011
(1988)

Article Doi