99679-74-0

Upstream product

• 34299-66-6 methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 99679-75-1 Methyl-4,6-O-benzyliden-2-desoxy-2-<(methoxycarbonyl)amino>-α-D-ribo-hexopyranosid-3-ulose 

Downstream Products

• 128657-58-9 methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 1291090-59-9 methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside 
• 1291090-68-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-deoxy-2-dimethylmaleimido-4,6-O-benzylidene-α-D-allopyranoside 
• 651736-01-5 methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 
• 99685-90-2 Methyl-4,6-O-benzyliden-2-desoxy-2-C-methyl-2-<(methoxycarbonyl)amino>-α-D-ribo-hexopyranosid-3-ulose 
• 526199-58-6 methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3,4,6-O-benzyl-α-D-glucopyranosyl]-(1->4)-α-D-glucopyranoside 
• 526199-56-4 methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl]-(1->4)-α-D-glucopyranoside 
• 526199-54-2 methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl]-(1->4)-α-D-glucopyranoside 
• 526199-52-0 methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside 
• 526199-57-5 methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside 
• 165399-19-9 Methyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-methoxycarbonylamino-α-D-glucopyranoside 

Relevant academic research and scientific papers

Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide

We present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido-d-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained.

Highly enantioselective diethylzinc addition to aldehydes catalyzed by D-glucosamine derivatives

Synthesis of α-hydroxy sulfonamides derived from D-glucosamine and their application as ligands in the titanium tetraisopropoxide-promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes is presented. The reaction is highly enantioselective and enantiomeric excesses of up to 97% for benzaldehyde and 88% for n-hexanal were obtained.

Synthesis of D-erythro-sphingosine from D-glucosamine

D-erythro-Sphingosine (1) was synthesized from D-glucosamine (2) as a chiral pool through stereoinversion of the C(3)-hydroxyl group via an oxidation-reduction sequence, transformation to the erythro-amino-alcohol chiron (9) protected as the oxazolidinone, and elongation of the side chain at the C(6)-position of the derived chloride (12).

Syntheses of optically active, unusual, and biologically important hydroxy-amino acids from d-glucosamine

Manipulation of D-glucosamine as a chiral pool including stereoinversion of the C3-hydroxyl group, degradation of the C6-carbon, and/or one carbon homologation at the C1-position realized chiral syntheses of (2S,3S)-dihydroxy-(4S)-amino acid moieties, important structural components of a gastroprotective substance AI-77-B and a group of antitumor substances calyculins.

Stereocontrolled synthesis of (-)-allosamizoline using D-glucosamine as a chiral template

(-)-Allosamizoline (1), a core component of novel insect chitinase inhibitor, allosamidin (2), was stereoselectively synthesized from D-glucosamine (3), using an efficient ring contraction reaction as a key step.