143169-52-2

Upstream product

• 185462-82-2 (+)-tert-butyl (1R,2S)-1-(tert-butoxycarbonylamino)-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate 
• 143169-43-1 (1R,2S)-(+)-tert-butyl 2-(acetoxymethyl)-1-cyclopropane-1-carboxylate 
• 143234-52-0 (1R,2S)-(+)-tert-butyl 1--2-(hydroxymethyl)cyclopropane-1-carboxylate 
• 143169-44-2 (2R,3S)-(+)-N-(tert-butoxycarbonyl)-O-tert-butyl-2,3-methanomethionine 

Relevant academic research and scientific papers

Large scale synthesis of N-protected 2,3-methanomethionine stereoisomers

Three stereoisomers of N-protected forms of 2,3-methanomethionine (cyclopropyl derivatives of methionine, or 'cyclo-Met') were prepared. Two of the syntheses developed involved diol (S)-1, which was more easily obtained from L-gulono-1,4-lactone than via juxtaposition of the benzyl protection of (R)-1. The cis-cyclo-Met derivative (cis refers to the orientation of the side chain relative to the amino functionality), FMOC-(2R,3S)-cyclo-Met, was obtained via a route based on a previous synthesis of (2R,3S)-cyclo-Met from the lactone 3, but the protected trans-cyclo-Met, BOC-(2S,3S)-cyclo-Met, was obtained via an improved procedure that does not involve lactone 3.