2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE

Details:

2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Chemical Properties
Melting point     151-156 °C
Boiling point     672.4±55.0 °C(Predicted)
density     1.22
storage temp.     Sealed in dry,Store in freezer, under -20°C
pka    11.87±0.70(Predicted)
Water Solubility     Soluble in CHCl3. Insoluble in water.
LogP    5.9 at 20℃ and pH6.5
CAS DataBase Reference    6564-72-3(CAS DataBase Reference)

2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a selectively protected intermediate, where the anomeric 1-O-hydroxyl group is free. This hemiacetal has been used successfully as an intermediate for glucosylation couplings, where it was converted into 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate using trichloroacetonitrile in the presence of a base such as potassium carbonate and DBU.
Importantly, this imidate donor with no neighbouring participating groups is commonly used for the selective formation of glucosides. 2,3,4,6-tetra-O-benzyl-D-glucopyranose can also be oxidized to the lactone, or reduced to give the open chain form.
Additionally, 2,3,4,6-tetra-O-benzyl-D-glucopyranose can be used for the preparation of glucono-1,5-lactone hydrazine, which was used, in-turn, to form a glucosylidene-spirocyclopropane.

It is the intermediate of Voglibose/Dapagliflozin. An important D-glucopyranose derivative for glucosylations and other reactions 1,2; Preparation of the α-glucopyranosyl chloride, synthesis of 1-C-α-D-glucopyranose derivatives.

Eye ContactRinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. Get medical attention. Skin ContactWash off immediately with plenty of water for at least 15 minutes. Get medical attention immediately if symptoms occur.InhalationRemove to fresh air. Get medical attention immediately if symptoms occur.IngestionClean mouth with water and drink afterwards plenty of water. Get medical attention if symptoms occur. Most important symptoms and effectsNone reasonably foreseeable.Self-Protection of the First AiderNo special precautions required. Notes to PhysicianTreat symptomatically.

Properties: It is a white to offwhite powder or crystalline solid. Insoluble in water£¬slightly soluble in dioxane and soluble in toluene etc.
Uses:This product is an important pharmaceutical intermediates and be used in synthesis voglibose, miglitol, dapagliflozin, and such as valienamine moiety of acarbose, bicyclic spiroacetal unsaturated glucoside of avermectin subunit, methoxy substituted THF synthons of annonaceous aeetogenins, serotype O-antigen oligosaccharides of shigella flexneri, phthalocyanine-glycoconjugates for photodynamic therapy, sugar-drug conjugate for molecular targeted therapies and so on. It also be used to synthesize some bioactive substance, for example, nojirimycin, aminocyclopentitol and tetrahydroimidazopyridines with glycosidase inhibitory activity, aspalathin with plasma glucose-lowering properties, rebeccamycin and glucosylisophosphoramide mustard with anti-tumor activity diosgenin analogue with anticancer activity to cervicouterine, ferrocen-tetrabenzyl glucose conjugate with antimalarial activity, bicyclic carbohydrates possessed activity against Leishmania donovani, glucopyranosyl phosphocholine with antifungal active, flavone glycoside with antioxidant and neuroprotective activities, aza-inositol with protein kinase B inhibitory activity, glucogallin with aldose reductase inhibitory activity, and glucosyl-2-azetidinone with cholesterol absorption inhibitory activity. This product is also used in synthesis arbutin, carminic acid, methoxyphenyl di-D-glucopyranoside as cryoprotectant, 1-O-octyl-D-glucitol as ice recrystallization inhibitor, alkyl glucoside surfactant, amphiphilicity block polymer in ink composition, metallofullerene glycoconjugates and the like. In addition, this product is also used as synthon of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone, trehalose, disaccharides, glycopeptides, pseudo-fructose, trehazolamine, septanoside, C-glycoside, various glycosylation donors such as 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl trichloroacetimidate, 1-deoxy-1-halo / thio / thiop