2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Product Name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- CAS No.
- 4132-28-9
- Chemical Name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Synonyms
- (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol;2,3,4, 6-4-o-benzyl-d-pyranoglucose;ucopyranose;Voglibose Impurity 4;2,3,4,6-Tetra-O-benz;Garlic oil 8000-78-0;benzyl-D-glucopyranose;Voglibose Intermediates;2,3,4,6-TETRABENZYL-D-GLUCOSE;Tetra-O-benzyl-D-glucopyranose
- CBNumber
- CB7194124
- Molecular Formula
- C34H36O6
- Formula Weight
- 540.65
- MOL File
- 4132-28-9.mol
2,3,4,6-Tetra-O-benzyl-D-glucopyranose Property
- 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
- InChI
- InChI=1S/C34H36O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-35H,21-25H2/t30-,31-,32+,33-,34?/m1/s1
- 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
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36-24/25
- WGK Germany
- 3
- HS Code
- 29400090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 86730
- Product name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Purity
- ≥98.0% (TLC)
- Packaging
- 1g
- Price
- $26
- Updated
- 2024/03/01
- Product number
- 86730
- Product name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Purity
- ≥98.0% (TLC)
- Packaging
- 5g
- Price
- $60.5
- Updated
- 2024/03/01
- Product number
- T1914
- Product name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Purity
- >97.0%(HPLC)
- Packaging
- 1g
- Price
- $43
- Updated
- 2024/03/01
- Product number
- T1914
- Product name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
- Purity
- >97.0%(HPLC)
- Packaging
- 5g
- Price
- $117
- Updated
- 2024/03/01
- Product number
- H27888
- Product name
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose, 98+%
- Packaging
- 1g
- Price
- $45.65
- Updated
- 2024/03/01
2,3,4,6-Tetra-O-benzyl-D-glucopyranose Chemical Properties,Usage,Production
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.
2,3,4,6-Tetra-O-benzyl-D-glucopyranose Preparation Products And Raw materials
Raw materials
Preparation Products
2,3,4,6-Tetra-O-benzyl-D-glucopyranose Suppliers
- Tel
- 0714-6352055 15897769779
- Fax
- 0714-6352055
- sales@healthdaychem.com
- Country
- China
- ProdList
- 95
- Advantage
- 55
- Tel
- 0579-89172082 18720986928
- Fax
- 0579-89172082
- 191094223@qq.com
- Country
- China
- ProdList
- 65
- Advantage
- 58
- Tel
- 02557628056 15150681880
- order@pushengmedical.com
- Country
- China
- ProdList
- 267
- Advantage
- 58
- Tel
- 0536-7971999 18232719690
- Fax
- 0536-7971999
- sgjiasheng@hotmail.com
- Country
- China
- ProdList
- 388
- Advantage
- 58
- Tel
- 0531-61320525 15866703830
- 495745175@qq.com
- Country
- China
- ProdList
- 7990
- Advantage
- 58
- Tel
- +86-021-57256005 +86-15921811235
- chang@shjlchem.com
- Country
- China
- ProdList
- 9
- Advantage
- 58
- Tel
- 19567218739
- 1759672789@qq.com
- Country
- China
- ProdList
- 1215
- Advantage
- 58
- Tel
- 021-50182298 021-50180596
- Fax
- +86-21-57758967
- sales@boylechem.com
- Country
- China
- ProdList
- 2208
- Advantage
- 55
- Tel
- 010-82848833 400-666-7788
- Fax
- 86-10-82849933
- jkinfo@jkchemical.com
- Country
- China
- ProdList
- 96815
- Advantage
- 76
- Tel
- 021-61259108 18621169109
- Fax
- 86-21-61259102
- market03@meryer.com
- Country
- China
- ProdList
- 40228
- Advantage
- 62
View Lastest Price from 2,3,4,6-Tetra-O-benzyl-D-glucopyranose manufacturers
- Product
- 2,3,4,6-Tetra-O-Benzyl-D-Glucopyranose 4132-28-9
- Price
- US $0.00/Kg
- Min. Order
- 1Kg
- Purity
- 98%
- Supply Ability
- 20Ton
- Release date
- 2024-10-22
- Product
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 4132-28-9
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-11-18
- Product
- 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 4132-28-9
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 50000KG/month
- Release date
- 2024-08-30