175694-63-0

Upstream product

• 160002-55-1 methyl (1S,2R,1'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 
• 132970-32-2 methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate 
• 160002-56-2 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',3'-dioxolan-2'-thiocarbonyl-4'-yl)cyclopropanecarboxylate 
• 160002-54-0 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 
• 160002-53-9 methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate 

Downstream Products

• 175694-64-1 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-methanesulfonyloxymethylcyclopropanecarboxylate 
• 175694-69-6 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-methylthiomethylcyclopropanecarboxylate 
• 175694-68-5 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate 
• 151074-58-7 (1S,2R)-1-benzyloxycarbonylamino-2-chloromethyl-1-cyclopropanecarboxylic acid methyl ester 
• 143169-51-1 (-)-(Z)-2,3-methanomethionine 
• 106928-49-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate 
• 257878-07-2 (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-tert-butyldiphenylsilyloxymethyl-1-methanesulfonyloxycyclopropane 
• 257878-06-1 (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-tert-butyldiphenylsilyloxymethyl-cyclopropane 
• 257878-08-3 (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-tert-butyldiphenylsilyloxymethyl-1-methylcyclopropane 
• 250225-64-0 (1S,2R)-(+)-1-N-benzyloxycarbonylamino-1,2,-bis(hydroxymethyl)cyclopropane 
• 171513-98-7 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate 
• 151074-57-6 (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2,3-methanohomoserine, (-)-(Z)-2,3-methanomethionine, and (2S,3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in turn, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in side-chain functionalization to the respective target molecules are discussed.