16895-86-6

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 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 
• 616-38-6 carbonic acid dimethyl ester 
• 105-58-8 Diethyl carbonate 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 79-22-1 methyl chloroformate 
• 100-39-0 benzyl bromide 

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 
• 14199-63-4 1-deoxymannojirimycin 
• 98260-69-6 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol 
• 53185-12-9 D-fagomine 
• 98260-66-3 methyl 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-α-D-lyxo-hexofuranoside 
• 98260-71-0 (2R,3R,4S,5R)-3-Benzyloxy-4-hydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 131053-26-4 (2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 98260-68-5 N-benzyloxycarbonyl-4-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 98260-59-4 Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester 
• 113000-80-9 (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester 
• 1332835-24-1 benzyl 2-azido-3-O-benzyl-2-deoxy-α-D-manofuranoside 
• 1332835-23-0 benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-mannofuranoside 
• 119870-63-2 benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-5-O-methyl-α-D-mannofuranoside 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized fro

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.