471891-15-3

Upstream product

• 471891-12-0 Benzoic acid (2R,4aR,6S,7R,8R,8aR)-7-azido-2-phenyl-8-trifluoromethanesulfonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 471891-13-1 2-azido-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl benzoate 
• 329038-46-2 2-azido-1-O-benzoyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 93-97-0 benzoic acid anhydride 
• 100-39-0 benzyl bromide 
• 471891-14-2 Benzoic acid (2R,4aR,6S,7R,8S,8aS)-7-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 

Downstream Products

• 877380-41-1 2-azido-3,4-di-O-benzyl-2-deoxy-6-Z-(1-dodecenylidene)-β-D-allopyranosyl benzoate 
• 877380-43-3 (2S,3S,4R,5R,6Z)-2-azido-3,4-dibenzyloxy-6-octadecene-1,5-diol 
• 877380-42-2 2-azido-3,4-di-O-benzyl-2-deoxy-6-Z-(1-dodecenylidene)-D-allopyranose 
• 471891-16-4 5-azido-5-deoxy-3,4-di-O-benzyl-L-allitol 

Relevant academic research and scientific papers

Metal trifluoromethanesulfonate-catalyzed regioselective reductive ring opening of benzylidene acetals

A systematic study of various metal trifluoromethanesulfonates as efficient catalysts in the regioselective reductive ring opening of benzylidene acetals is described, including the effects of solvents, reducing agents, and temperature. These catalysts are found to be effective in cleaving the 4,6-O-acetal rings of hexopyranosides at either O4 or O6, respectively. When used in conjunction with a 1 M solution of BH3.THF in THF without extra addition of any solvent, it affects the ring fission at the O6 position to generate the corresponding primary alcohols, whereas O4-opening takes place in acetonitrile in the presence of dimethylethylsilane as the reductant leading to the secondary hydroxyl derivatives in high selectivity and yields. These methodologies can be applied to a wide range of substrates containing various functional groups.

A concise synthesis of tetrahydroxy-LCB, α-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks

The total syntheses of tetrahydroxy-LCB 1, α-galactosyl ceramide 2, and 1,4-dideoxy-1,4-imino-L-ribitol 3 via D-allosamine derivatives as common synthons are described here.

Synthesis of D-ribo-C18-phytosphingosine from D-glucosamine via the D-allosamine derivatives as key intermediates

A straightforward synthesis of D-ribo-C18-phytosphingosine from D-glucosamine hydrochloride in ten steps in 18.4% overall yield via the D-allosamine derivatives as key intermediates is described here.