| Identification | More | [Name]
2,3,4,6-Tetra-O-benzyl-D-glucopyranose | [CAS]
4132-28-9 | [Synonyms]
2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE
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
2,3,4,6-Tetra-O-benzyl-D-glucopyranose, 98+%
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose ,97% | [EINECS(EC#)]
609-908-7 | [Molecular Formula]
C34H36O6 | [MDL Number]
MFCD00023849 | [Molecular Weight]
540.65 | [MOL File]
4132-28-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystaline Solid | [Melting point ]
145-149 °C(lit.)
| [Boiling point ]
672.4±55.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in chloroform | [form ]
Solid | [pka]
11.87±0.70(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280-P271 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29400090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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. | [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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