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| | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose Basic information |
| Product Name: | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose | | Synonyms: | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(for Voglibose);2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE, 98%, MIXTURE OF ANOMERS;3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;2,3,4,6-TETRA-O-BENZYL-D -GLUCOPYRANOSE CRYSTALLINE;2,3,4,6-Tetra-O-benzyl-D-glucopyranose;2,3,4,6-TETRABENZYL-D-GLUCOSE;D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-;2,3,4,6-TETRA-O-BENZYL-A-D-GLUCOPYRANOSIDE | | CAS: | 4132-28-9 | | MF: | C34H36O6 | | MW: | 540.65 | | EINECS: | 609-908-7 | | Product Categories: | Halogenated Heterocycles ,Pyrazoles;Biochemistry;Glucose;O-Substituted Sugars;Sugars;aldehydes;Carbohydrates & Derivatives;Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Monosaccharide;13C & 2H Sugars;Glycon Biochem;Specialty Synthesis;Monosaccharides;Carbohydrate Synthesis | | Mol File: | 4132-28-9.mol |  |
| | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose Chemical Properties |
| Melting point | 145-149 °C(lit.) | | Boiling point | 672.4±55.0 °C(Predicted) | | density | 1.22±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | Soluble in chloroform | | pka | 11.87±0.70(Predicted) | | form | Solid | | color | White to Off-White | | optical activity | [α]20/D +49±2°, c = 2% in dioxane | | InChIKey | OGOMAWHSXRDAKZ-BKJHVTENSA-N | | SMILES | OC1O[C@H](COCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H]1OCC1=CC=CC=C1 | | CAS DataBase Reference | 4132-28-9(CAS DataBase Reference) |
| | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose Usage And Synthesis |
| Description | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is an important D-glucopyranose derivative, which is often used as a pharmaceutical intermediate in the synthesis of derivatives for the treatment of Alzheimer's disease, diabetes, and cancer. | | Chemical Properties | White Crystaline Solid | | Uses | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (cas# 4132-28-9) is a compound useful in organic synthesis. For example, it enables the preparation of α-glucopyranosyl chloride as well as 1-C-α-D-glucopyranosyl derivatives; it can also be used in the preparation of important D-glucopyranosyl derivatives for glucosylation and other reactions. | | Application | After activation with trifluoroacetic anhydride, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose reacts with various silyl enol ethers or allyl silanes in the presence of Lewis acids to generate α-configured C-D-glucopyranosyl derivatives, and reacts with activated aromatic nucleophiles to generate the corresponding β-anomers[2]. It can also be used to synthesize the antibiotic (+)-nojirimycin[3]. | | Reactions | The coupling reaction of 2,3,4,6-tetra-O-benzyl-1-C-phenyl-α-D-glucopyranose with 2,3,4,6-tetra-O-benzyl-D-glucopyranose, in the presence of 5 mol% bismuth(III) triflate in dichloromethane at 0 °C, could synthesize 2,3,4,6-tetra-O-benzyl-1-C-phenyl-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside[1].
 | | Synthesis | Add 19.4g of 2,3,4,6-tetra-O-benzyl-β-D-glucosinolate to 500mL of acetone, and add 18.7g of N-bromosuccinyl in batches with stirring Imine (NBS), after the addition, react at 25°C for 0.5h. Most of the acetone was evaporated under reduced pressure, and a white solid was precipitated, which was diluted by adding 200 mL of 1mol/L hydrochloric acid and allowed to stand at -18°C for 3h. After suction filtration, the filter cake was washed with cold absolute ethanol, and recrystallized with absolute ethanol-cyclohexane to obtain 15.6 g of white flocculent solid 2,3,4,6-Tetra-O-benzyl-D-glucopyranose with a yield of 96.6%. | | References | [1] T. Yamanoi, Yoshiki Oda, R. Inoue. “2,3,4,6-Tetra-O-benzyl-1-C-phenyl-α-D-glucopyranosyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside.” Molbank 35 1 (2012).
[2] P. ALLEVI. The first direct method for C-glucopyranosyl derivatization of 2,3,4,6-tetra-O-benzyl-D-glucopyranose[J]. Journal of The Chemical Society, Chemical Communications, 1987. DOI:10.1039/C39870001245.
[3] STéPHANE MOUTEL M. S. Synthesis of (+)-nojirimycin from 2,3,4,6-tetra-O-benzyl-D-glucopyranose[J]. Journal of The Chemical Society-perkin Transactions 1, 1999. DOI:10.1039/A901811E.
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| | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose Preparation Products And Raw materials |
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