66963-60-8

Upstream product

• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 111-96-6 diethylene glycol dimethyl ether 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 882689-03-4 Benzoic acid (S)-2-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 868078-60-8 (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole 

Downstream Products

• 1350618-70-0 1,6-anhydro-2,4-di-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 1350618-82-4 3-O-benzyl-1-thio-α-D-glucopyranose 
• 498-07-7 levoglucosan 
• 23567-05-7 1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-glucopyranose 

Relevant academic research and scientific papers

Regioselective de-O-benzylation of monosaccharides

Poly-O-benzylated sugars are regioselectively debenzylated using CrCl2/LiI in moist EtOAc. A predictive, three-point coordination model is proposed.

PURE HEPTASULFATED DISACCHARIDES HAVING IMPROVED ORAL BIOAVAILABILITY

Hypersulfated disaccharides with utility in asthma or asthma related disorders are disclosed. The heptasulfated disaccharides administered orally have comparable bioavailability to the intravenous administered dosage form.

Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars

Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).

DISACCHARIDE COMPOUNDS

Disaccharide compounds used as building blocks for making heparin and heparan sulfate oligosaccharides. Also disclosed are methods for making these disaccharide compounds.

Heparin oligosaccharides

The present invention provides composition and methods for the synthesis of low molecular weight heparins and heparinoids. The present invention also provides compositions having substantially homogenous populations of desired heparin molecules, or molecu