165399-19-9

Upstream product

• 99679-74-0 2-amino-4,6-O-benzylidene-3-O-(N-propylcarbamoyl)-2-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 34299-66-6 methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside 
• 99679-74-0 Methyl-4,6-O-benzyliden-2-desoxy-2-<(methoxycarbonyl)amino>-α-D-glucopyranosid 

Downstream Products

• 139573-22-1 Methyl 2-amino-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 252055-28-0 3-O-benzylallosamizoline 
• 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 
• 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 
• 139573-28-7 [(3aS,4R,5R,7aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3a,4,5,7a-tetrahydro-benzooxazol-2-yl]-dimethyl-amine 
• 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 
• 139573-27-6 3-[(1S,5S,6R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-oxo-cyclohex-2-enyl]-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 
• 139573-25-4 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 
• 139573-26-5 3-[(2S,3R,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl]-1,1-dimethyl-urea 
• 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 
• 114673-96-0 (-)-allosamizoline hydrochloride 

Relevant academic research and scientific papers

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.

PREPARATION OF A HIGHLY FUNCTIONALIZED CYCLOPENTANE DERIVATIVE SUITABLE FOR THE SYNTHESIS OF ALLOSAMIDIN ANALOGS

Methyl 3,6-di-O-benzyl-4-O-benzoyl-2-deoxy-2-methoxycarbonylamino-α-D-glucopyranoside (8) was prepared from D-glucosamine via its 4,6-O-benzylidene derivative.The methyl glycoside moiety of 8 was hydrolyzed in the presence of d-camphorsulfonic acid in ace