160002-53-9

Upstream product

• 186581-53-3 diazomethane 
• 132970-32-2 methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 

Downstream Products

• 175694-64-1 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-methanesulfonyloxymethylcyclopropanecarboxylate 
• 175694-69-6 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-methylthiomethylcyclopropanecarboxylate 
• 175694-63-0 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate 
• 175694-68-5 methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate 
• 171513-98-7 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate 
• 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 
• 151074-57-6 (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester 
• 151074-58-7 (1S,2R)-1-benzyloxycarbonylamino-2-chloromethyl-1-cyclopropanecarboxylic acid methyl ester 
• 143169-51-1 (-)-(Z)-2,3-methanomethionine 
• 65878-52-6 (+)-(1S,2R)-allocoronamic acid 
• 106928-49-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate 
• 160002-54-0 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 

Relevant academic research and scientific papers

Highly efficient and stereocontrolled synthetic route to enantiopure ACC derivatives: Synthesis of (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester

Highly diastereoselective cyclopropanation of a chiral α,β-dehydroamino acid derivative, obtained from D-mannitol, leads to a single isomer which has been transformed into the title compound in 65% overall yield. This product can be a useful intermediate

1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: The origin of the π-facial diastereoselection

The stereochemical outcome of diazomethane cycloadditions to several chiral electron-deficient olefins has been investigated in order to establish the origin of the π-facial diastereoselection. Nitro olefins, vinyl sulfones, enoates, and 2-amino enoates h

Synthesis and photochemical decomposition of pyrazolines from homochiral amino pentenoates. A laser flash-photolysis study

Optically pure pyrazolines have been synthesized by cycloaddition of diazomethane to homochiral amino pentenoates, facial diastereoselectivity being the opposite depending on the Z/E stereochemistry of the precursors. Photo-decomposition of these pyrazolines to the corresponding cyclopropanes has been shown to occur stereospecifically and has been studied in order to find the optimal conditions and to establish the influence of sensitizers. The transient behaviour of the pyrazoline triplet state has been analyzed by laser flash photolysis either after direct excitation or after energy transfer from benzophenone.

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.