162338-26-3

Upstream product

• 162600-52-4 methyl (4R,5S)-4,5-(isopropylidenedioxy)-2(E)-hexenoate 
• 100-46-9 benzylamine 
• 63357-08-4 methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate 
• 183625-29-8 methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 
• 67315-16-6 methyl (4S,5S)-(4,5)-epoxy-2(E)-hexenoate 
• 103-50-4 dibenzyl ether 
• 100423-92-5 (S)-3-Nitro-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 

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).

Formal syntheses of N-trifluoroacetyl-L-acosamine and N-trifluoroacetyl-L-daunosamine from an achiral precursor, methyl sorbate

N-Trifluoroacetyl-L-acosamine 20 and N-trifluoroacetyl-L-daunosamine 21 were formally synthesized from an achiral precursor, methyl sorbate 4, based on enzymatic chiral induction and diastereoselective 1,4-conjugated addition of benzylamine to the olefini