103588-86-9

Upstream product

• 87791-58-0 azetidinone-4-carboxylic acid benzyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 610273-49-9 4-benzoyloxymethyl-N-(t-butyldimethylsilyl)-2-azetidinone 
• 337522-48-2 1-benzyl-4-(tert-butyldimethylsilyloxymethyl)azetidin-2-one 
• 188304-72-5 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid 

Relevant academic research and scientific papers

Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone

The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78°C into amide anion by N-O migration of the silyl protecting group. The occurrence of this intermediate was proved by quenching with benzyl bromide and phenethyl chloroformate, giving respectively N-benzyl (4) and N-(phenethyloxycarbonyl) (6) derivatives of 4-(t-butyldimethylsilyloxy)methyl-2-azetidinone.

Antibiotic synthesis

A method of preparing intermediates for carbapenem antibiotics characterized by treating a N-deprotected acetoxy conpound of the formula: STR1 in the presence of a Lewis acid or a silylating agent to yeild an intermediate; and cyclizing the intermediate in the presence of rhodium (II) acetate to form a bicyclic ketoester.