194229-45-3

Upstream product

• 194229-42-0 methyl (3S,4S,5S)-3-benzylamino-4,5-epoxyhexanoate 
• 100-46-9 benzylamine 
• 67315-16-6 methyl (4S,5S)-(4,5)-epoxy-2(E)-hexenoate 

Downstream Products

• 100484-30-8 (3S,4S,5R)-3-benzamido-5-hydroxy-4-hexanolide 
• 761362-01-0 (4S,5S)-4-Amino-5-((R)-1-hydroxy-ethyl)-dihydro-furan-2-one 
• 17016-65-8 N-((2R,3S,4S)-3,6-Dihydroxy-2-methyl-tetrahydro-pyran-4-yl)-benzamide 

Relevant academic research and scientific papers

Chemoenzymatic syntheses of N-trifluoroacetyl-L-daunosamine, N-trifluoroacetyl-L-acosamine, N-benzoyl-D-acosamine, and N-benzoyl-D-ristosamine from an achiral precursor, methyl sorbate

A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate 8a followed by lactonization under acidic condition proceeds to the formal total syntheses of L-daunosamine 4 and L-acosamine 2. On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate 5 and the subsequent intramolecular nucleophilic attack by the ester carbonyl group on the epoxy ring of the substrates leads to the formal total syntheses of D-acosamine 2 and D-ristosamine 1. Copyright (C) 2000 Elsevier Science Ltd.

Total syntheses of N-trifluoroacetyl-L-daunosamine, N-trifluoroacetyl-L-acosamine, N-benzoyl-D-acosamine, and N-benzoyl-D-ristosamine from an achiral precursor, methyl sorbate

A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate (12) followed by lactonization under acidic condition proceeds formally to the total syntheses of L-daunasamine (1) and L-acosamine (2). On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate (4) and the subsequent intramolecular nucleophilic attack by ester carbonyl group against epoxy ring of the substrates leads to the formal total syntheses of D-acosamine (2) and D-ristosamine (3).