100568-97-6

Upstream product

• 63357-08-4 methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate 
• 162600-52-4 methyl (4R,5S)-4,5-(isopropylidenedioxy)-2(E)-hexenoate 
• 98-88-4 benzoyl chloride 
• 75712-49-1 (S)-3-Amino-3-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 
• 111524-15-3 N-[((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene]((1R)-1-phenylethyl)amine N-oxide 
• 111524-16-4 N-<<(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl>methylene>benzhydrylamine N-oxide 
• 111612-92-1 (4S,5S)-(Z)-N-(2,2,5-trimethyl-1,3-dioxolan-4-yl)methylenebenzylamine N-oxide 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 111524-24-4 methyl (3S,4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111612-93-2 (Z)-((4R)-trans-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene((1S)-1-phenylethyl)amino N-oxide 
• 78513-04-9 (4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester 
• 85099-89-4 (S,S)-2,2-dimethyl-4-benzyloxymethyl-5-methyl-1,3-dioxolane 

Downstream Products

• 75712-56-0 (3S,4R,5S)-arabino-3-benzoylamino-2,3,6-trideoxyaldonic acid γ-lactone 
• 81176-31-0 N-Benzoyl-L-daunosamine 
• 82266-95-3 (+)-lyxo-3-(Benzoylamino)-2,3,6-trideoxyhexanoic acid γ-lactone 

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

THE CHEMISTRY OF SILYLATED KETENE ACETALS: AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF N-BENZOYL L-DAUNOSAMINE

N-Benzoyl L-daunosamine was synthesized with high stereoselectivity utilizing a 1,3-addition of ketene silyl acetal (3a) to the chiral nitrone, (Z)-((4R)-trans-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene((1S)-1-phenylethyl)amine N-oxide (4c) accompanied by a silyl group-transfer in acetonitrile under mild conditions.