β-Lactam antifungals. II. Enantiocontrolled synthesis of (2R,5S)-2-hydroxymethyl-1-carbapenam, the carba-analog of a clavam antifungal

DOI: 10.1248/cpb.39.2813

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2813 - 2818 (1991)

Update date:2022-07-30

Topics:

Authors:

Konosu Konosu

Furukawa

Hata Hata

Oida Oida

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

Article abstract of DOI:10.1248/cpb.39.2813

(2R,5S)-2-Hydroxymethyl-1-carbapenam (3), the carba-analog of an antifungal β-lactam (2R,5S)-2-(hydroxymethyl)clavam (1), was synthesized in an enantiocontrolled manner, starting from the coupling reaction of an optically active phthalimido-acetate (3S,4S)-4 and an allylsilane 7, followed by removal of the phthalimido group that was crucial for asymmetric induction. Hydroboration, protecting-group interconversion, and cyclization gave 3 stereoselectively.

Full text of DOI:10.1248/cpb.39.2813

NII-Electronic Library Service

Products guided by the article

Product name:(3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-3-phthalimido-2-azetidinone

Cas No:139747-94-7

R&D Labs maybe for 139747-94-7

Advanced Biotech

Contact:+1-973-357-0577

Address:10 Taft Rd.
ZHEJIANG CHEMICAL INDUSTRY INSTITUTE TECHNOLOGY CO.,LTD(expird)

Contact:86-575-82730298

Address:shangyu
Nantong Kaixin Pharma Chemical Co.,Ltd.

Contact:86-513-85250786

Address:2-1103 Huachen Mansion, 111 Gongnong Road,Nantong, Jiangsu, China
jintan yufan Medicine Raw materials Co.,Ltd.(expird)

Contact:86-519-82808282

Address:6th,Jincheng Huangzhuang
LIANYUNGANG YC FINE CHEMICAL CO., LTD

Contact:+86-518-858 99188

Address:Shangdong Modern Bldg, South Greenpark Road, Lianyungang, Jiangsu Pro. China

Relevant to this article

Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A

Doi:10.1002/chem.201200517
(2012)
Palladium (II)-catalysed intramolecular C–H functionalizations: Efficient synthesis of kealiinine C and analogues

Doi:10.1016/j.mcat.2018.06.007
(2018)
Introduction of a non-natural amino acid into a nonribosomal peptide antibiotic by modification of adenylation domain specificity

Doi:10.1002/anie.201202043
(2012)
Novel 4,4-bis(trifluoromethyl) imidazolines as stereospecific and orally active acyl CoA: Cholesterol acyltransferase (ACAT) inhibitors and antihypercholesterolemic agents

Doi:10.1016/0960-894X(96)00137-0
(1996)
Synthesis of maleopimaric and citraconopimaric acids N-[3-(pyrimidin-2-yl) aryl]amides

Doi:10.1134/S1070428012080143
()
Catalyst and solvent-free, ultrasound promoted rapid protocol for the one-pot synthesis of α-aminophosphonates at room temperature

Doi:10.1016/j.tetlet.2012.07.123
(2012)

Article Doi