72658-70-9

Upstream product

• 72658-68-5 [2-(2-Iodo-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester 
• 908094-04-2 phenyldiazomethane 
• 72658-67-4 tert-butyl 2-(2-iodoethyl)-4-oxo-1-azetidineacetate 
• 72658-65-2 tert-butyl 2-(2-hydroxyethyl)-4-oxo-1-azetidineacetate 
• 72658-63-0 tert-butyl 2-(2-acetoxyvinyl)-4-oxo-1-azetidineacetate 
• 72658-64-1 tert-butyl 2-(2-acetoxyethyl)-4-oxo-1-azetidineacetate 
• 72658-66-3 tert-butyl 2-<2-<(methanesulfonyl)oxy>ethyl>-4-oxo-1-azetidineacetate 
• 67501-71-7 benzyl 7-oxo-1-azabicyclo[3.2.0] hept-2-ene-2-carboxylate 
• 79669-46-8 (2-Allyl-4-oxo-azetidin-1-yl)-chloro-acetic acid benzyl ester 
• 68485-52-9 4-allylazetidin-2-one 
• 68485-53-0 4-allyl-1-(1-hydroxy-1-benzyloxycarbonylmethyl)-azetidin-2-one 
• 64221-82-5 4-(2-acetoxy-(E)-vinyl)-2-azetidinone 
• 72658-61-8 tert-butyl 2-(2-acetoxyvinyl)-α-hydroxy-4-oxo-1-azetidineacetate 
• 72658-62-9 tert-butyl 2-(2-acetoxyvinyl)-α-chloro-4-oxo-1-azetidineacetate 

Relevant academic research and scientific papers

Olivanic Acid Analogues. Part 1. Total Synthesis of the 7-Oxo-1-azabicyclohept-2-ene-2-carboxylate System and Some Related β-Lactams

4-Allylazetidin-2-one, prepared from penta-1,4-diene and chlorosulphonyl isocyanate, has been used to synthesise the parent 7-oxo-1-azabicyclohept-2-ene-2-carboxylate system of the naturally occurring olivanic acids, using an intramolecular Wittig reaction to construct the 2,3-double bond.Cyclisation of ketones derived from the 4-allyl grouping produced 3-substituted derivatives, while use of the azetidin-2-one prepared from hexa-1,5-diene and chlorosulphonyl isocyanate has given the homologous 8-oxo-1-azabicyclooct-2-ene system.

Thienamycin Total Synthesis. 2. Model Studies - Synthesis of a Simple 2-(Alkylthio)carbapen-2-em

Model studies directed toward the total synthesis of (+/-)-thienamycin are described which have resulted in the preparation of the benzyl ester of (+/-)-2-(methylthio)carbapen-2-em-3-carboxylic acid (2).Azetidinone 3 was converted into thioenolether 24 via thioacetal 6.Bromination of 24 followed by treatment with base afforded the key bicyclic intermediate 25.Dehydrobromination, decarbalkoxylation, and isomerization of the double bond then yielded the desired model compound 2.The synthesis of carbapenams 19a,b (R = t-Bu and Bz) from azetidinone 11 is also described.