139573-22-1

Upstream product

• 99679-74-0 2-amino-4,6-O-benzylidene-3-O-(N-propylcarbamoyl)-2-deoxy-α-D-glucopyranoside 
• 93000-11-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 34299-66-6 methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside 
• 144789-65-1 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 165399-19-9 Methyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-methoxycarbonylamino-α-D-glucopyranoside 

Downstream Products

• 385784-50-9 methyl 2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 162678-87-7 Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 175978-55-9 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 501088-17-1 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 114673-96-0 (-)-allosamizoline hydrochloride 
• 139582-59-5 Toluene-4-sulfonic acid (3aR,4R,5R,6R,7R,7aR)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-6-hydroxy-3a,4,5,6,7,7a-hexahydro-benzooxazol-7-yl ester 
• 139573-26-5 3-[(2S,3R,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl]-1,1-dimethyl-urea 
• 139573-25-4 3-[(2S,3R,4R,5S,6S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-yl]-1,1-dimethyl-urea 
• 139573-29-8 (3aR,4R,5R,6S,7R,7aR)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-3a,4,5,6,7,7a-hexahydro-benzooxazole-6,7-diol 
• 139573-27-6 3-[(1S,5S,6R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-oxo-cyclohex-2-enyl]-1,1-dimethyl-urea 
• 139573-30-1 [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol 
• 139573-28-7 [(3aS,4R,5R,7aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3a,4,5,7a-tetrahydro-benzooxazol-2-yl]-dimethyl-amine 
• 139573-23-2 3-((2S,3R,4R,5S,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-1,1-dimethyl-urea 
• 139573-24-3 3-((2S,3R,4R,5S,6S)-4-Benzyloxy-5-hydroxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-yl)-1,1-dimethyl-urea 

Relevant academic research and scientific papers

METHOD FOR PREPARING FULLY PROTECTION HEPARIN PENTASACCHARIDE AND INTERMEDIATE THEREOF

Disclosed is a process for chemically synthesizing a pharmaceutical intermediate, in particular to a novel intermediate and novel process for synthesizing an anticoagulant drug fondaparinux sodium intermediate - full protection heparin pentasaccharide. The process has a high reaction efficiency and a simple reaction operation, and enables the reaction intermediate to be easily purified, thus being suitable for the industrialized production of the full protection heparin pentasaccharide.

DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis

The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH2Cl2 or nitromethane in the presence of LiClO4. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl3, TMSOTf, or BF3·Et2O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO4 gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.

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.