16895-86-6

Basic information

• Product Name: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate
• Synonyms: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate
• CAS NO: 16895-86-6
• Molecular Weight: 336.342
• Mol File: 16895-86-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate(16895-86-6)
• EPA Substance Registry System: 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate(16895-86-6)

Safety Data

• Hazardous Substances Data: 16895-86-6(Hazardous Substances Data)

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 79-22-1 methyl chloroformate 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 105-58-8 Diethyl carbonate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 616-38-6 carbonic acid dimethyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 16895-87-7 methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate 
• 16895-88-8 methyl 3-O-benzyl-β-D-glucofuranoside-5,6-carbonate 
• 98260-65-2 methyl 5,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-L-gulofuranoside 
• 98260-64-1 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside 
• 98260-63-0 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside-5,6-carbonate 
• 98260-70-9 methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-mannofuranoside 
• 98260-67-4 methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 
• 98260-60-7 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-mannofuranoside 
• 98260-62-9 methyl 3-O-benzyl-2-O-trifluoromethanesulphonyl-α-D-glucofuranoside-5,6-carbonate 
• 98260-61-8 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-5-O-methanesulphonyl-α-D-mannofuranoside 
• 59920-31-9 2,5-dideoxy-2,5-imino-D-mannitol 
• 105285-30-1 methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 
• 98260-71-0 N-benzyloxycarbonyl-3-O-benzyyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 105265-97-2 methyl N-t-butyloxycarbonyl-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 

Relevant articles and documents

Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine from D-glucose

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Allylation of sugar diols under phase transfer conditions using potassium carbonate as a base. Unexpected formation of cyclic carbonates

Allylation of sugar vic-diols (with a primary and secondary OH groups) under the phase transfer conditions (allyl bromide, K2CO3, 18-crown-6, toluene) afforded a mixture of both monosubstituted allyl ethers and small amounts of the di-allyl derivative. Interestingly, the cyclic carbonate was also isolated from the post reaction mixture. Its formation may be explained by reaction of the di-allyl carbonate, formed in situ under the reaction conditions, with the 1,2-diol. The structure of mono-allylated isomers can be easily assigned from the chemical shift (δc) of the CH2OR group (for R = H; All).

Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mamnofuranoside as a divergent intermediate for the synthesis of polyhydroxylated piperidines and pyrrolidines: synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine]

The synthesis of methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (1) from D-glucose is reported; the conversions of (1) into derivatives of methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside (as precursors for the synthesis of polyhydroxylated piperidines) and into the hydroxylated pyrrrolidine, 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine] are described.