5372-53-2

Upstream product

• 551-16-6 6-aminopenicillanic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 85091-07-2 <2R,2'R,4'S>2-Benzyloxycarbonylamino-2-<5',5'-dimethyl-4'-diphenylmethylcarboxy-2'-thiazolidine>-ethanol 
• 95519-43-0 benzhydryl (2R,4S)-2-<(1S)-1-benzyloxycarbonylamino-2-bromoethyl>-5,5-dimethylthiazolidine-4-carboxylate 
• 95519-42-9 benzhydryl (2R,4S)-2-<(1S)-1-benzyloxycarbonylamino-2-chloroethyl>-5,5-dimethylthiazolidine-4-carboxylate 
• 85091-08-3 benzhydryl (4S)-5,5-dimethylthiazolidine-4-carboxylate 
• 85091-06-1 benzhydryl (3S,5R,6R)-6-benzyloxycarbonylaminopenicillanate 

Relevant academic research and scientific papers

Diborane Reduction of Penicillins: Preparation of 7-Deoxopenicillanic Acid

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.

Carbonic acid esters, and the preparation thereof and their use

Carbonic acid esters of the formula substituent(s) substituents(s) wherein R'1 is lower alkyl which may have substituent)s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituents)s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R'2 is benzotriazolyl which may have halogen; or a group represented by the formula: STR1 wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R'2 is a group represented by the formula: STR2 wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R'1 is ar(lower) alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano. A process for the protection of amino and/or imino groups in compounds containing them by reacting them with the aforementioned esters is also disclosed.

Oxime carbonates

Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group - containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed.