175694-64-1

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 151074-57-6 (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester 
• 175694-63-0 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate 
• 160002-53-9 methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate 
• 160002-54-0 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 
• 160002-56-2 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',3'-dioxolan-2'-thiocarbonyl-4'-yl)cyclopropanecarboxylate 
• 160002-55-1 methyl (1S,2R,1'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate 
• 160002-57-3 (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 

Downstream Products

• 106928-49-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate 
• 175694-68-5 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate 
• 250225-69-5 methyl (1S,2R)-2-[(6-amino-9H-purin-9-yl)methyl]-1-(benzyloxycarbonylamino)cyclopropanecarboxylate 
• 250225-70-8 (1S,2R)-2-[(6-amino-9H-purin-9-yl)methyl]-1-benzyloxycarbonylamino-2-hydroxymethylcyclopropane 
• 143169-51-1 (-)-(Z)-2,3-methanomethionine 
• 175694-69-6 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-methylthiomethylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Stereoselective synthesis of novel types of cyclopropyl carbocyclic nucleosides containing quaternary stereogenic centers

Versatile and stereocontrolled synthetic entries to novel types of cyclopropyl carbocyclic nucleosides are described. The target products have been synthesized from suitable cyclopropane precursors obtained, in turn, from olefinic compounds derived from D-glyceraldehyde as a chiral precursor. Selective manipulation of the functional groups has allowed the preparation of enantiopure nucleosides, some of them displaying opposite chirality. All these molecules contain a quaternary stereogenic carbon at C-1 or C-3 of the cyclopropane ring and bear an amino, a hydroxymethyl, or a methyl group as an additional substituent. In one instance, thymine is directly linked to the cyclopropane. A methylene unit serves as the spacer in the other synthesized nucleosides.

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.