85091-07-2Relevant academic research and scientific papers
Diborane Reduction of Penicillins: Preparation of 7-Deoxopenicillanic Acid
Sammes, Peter G.,Smith, Steven,Woolley, Geoffrey T.
, p. 2603 - 2610 (2007/10/02)
The reduction of 6β-acylamidopenicillanates with diborane is shown to proceed by opening of the β-lactam ring to produce the corresponding amino alcohols.The chemistry of the reduction product from benzhydryl 6β-benzyloxycarbonylaminopenicillanate has been explored, in paticular its reaction with methanolic potassium hydroxide; no azetidines are formed.Cyclisation of the amino alcohol prepared from methyl penicillanate may be effected either indirectly, via the corresponding bromide, or directly, by use of a modified Mitsunobu reaction, to produce methyl 7-deoxypenicillanate.
STUDIES IN PENICILLIN CHEMISTRY. ISOLATION AND CHARACTERISATION OF METHYL 3,3-DIMETHYL-6-HYDROXY-METHYL-8-OXO-4-THIA-1,7-DIAZABICYCLO-OCTANE (A) AND 4-HYDROXYMETHYL-7,7-DIMETHYL-6-THIA-3,8-DIAZABICYCLOOCTANE-2-ONE (B)
Petursson, Sigthor,Waley, Stephen G.
, p. 2465 - 2468 (2007/10/02)
Reduction of diphenylmethyl benzyloxypenicillinate with borane-tetrahydrofuran gives 2-benzyloxy-carbonylamino-2--ethanol (5) as the main product.Treatment of this compound with methanol
