2,3,4,6-Tetra-O-benzyl-D-glucopyranose
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2,3,4,6-Tetra-O-benzyl-D-glucopyranose ??
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- 145-149 °C(lit.)
- ?? ?
- 672.4±55.0 °C(Predicted)
- ??
- 1.22±0.1 g/cm3(Predicted)
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- Sealed in dry,Store in freezer, under -20°C
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- ?? ?? (pKa)
- 11.87±0.70(Predicted)
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- [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 ??????
- 4132-28-9(CAS DataBase Reference)
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- ?? ? ???? ?? (GHS)
| ??? ?? | Xi | ||
|---|---|---|---|
| ?? ???? ?? | 36/37/38 | ||
| ????? | 26-36-24/25 | ||
| WGK ?? | 3 | ||
| HS ?? | 29400090 | ||
| ???? ??? | 11 - Combustible Solids |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose C??? ??, ??, ??
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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.??? ??
White Crystaline Solid??
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.?? ??
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].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%.?? ??
[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.
2,3,4,6-Tetra-O-benzyl-D-glucopyranose ?? ?? ? ???
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2,3,4,6-Tetra-O-benzyl-D-glucopyranose ?? ??
???( 445)?? ??
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2,3,4,6-Tetra-O-benzyl-D-glucopyranose ?? ??:
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