ChemicalBook > CAS DataBase List > 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE

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

Product Name
2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE
CAS No.
6564-72-3
Chemical Name
2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE
Synonyms
Voglibose int;benzylglucopyranose;Tetrabenzyl glucose;Voglibose Impurity 1;Voglibose TBG IMpurity;Voglibose TBG impurities;Voglibose alpha-TBG Impurity;2,3,4,6-tetra-o-benzyl-d-glucose;6-Tetra-O-benzyl-D-glucopyranose;2,3,4,6-Tetra-o-benzyl-D-glucopyransoe
CBNumber
CB0234449
Molecular Formula
C34H36O6
Formula Weight
540.66
MOL File
6564-72-3.mol
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2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Property

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)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Alfa Aesar
Product number
H31595
Product name
2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranose, 98%
Packaging
1g
Price
$55.65
Updated
2024/03/01
Alfa Aesar
Product number
H31595
Product name
2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranose, 98%
Packaging
5g
Price
$180.65
Updated
2024/03/01
TRC
Product number
P992030
Product name
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose
Packaging
100mg
Price
$60
Updated
2021/12/16
TRC
Product number
P992030
Product name
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose
Packaging
500mg
Price
$90
Updated
2021/12/16
Usbiological
Product number
294905
Product name
2,3,4,6-Tetra-O-benzoyl-D-glucopyranose
Packaging
100mg
Price
$375
Updated
2021/12/16
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2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Chemical Properties,Usage,Production

Description

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.

Uses

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.

Synthesis

Octa-O-Dissolves benzyl sucrose or octa-O-allyl sucrose in an organic solvent with the addition of hydrochloric acid without prior chromatographic purification, allows it to react for 20-60 minutes at temperatures of 50-60 °C. and then cleans the end product formed by crystallization. (ethanol, isopropanol, acetone, benzene, toluene or mixtures thereof can be used as solvents).

2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Preparation Products And Raw materials

Raw materials

Preparation Products

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

Canada 2 China 228 Czech 1 France 1 Germany 7 India 7 Japan 1 Poland 1 Slovakia 1 Switzerland 4 The Netherlands 1 United Kingdom 8 United States 27 Global 289
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View Lastest Price from 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2,3,4,6-tetra-O-benzyl-D-glucopyranose 6564-72-3
Price
US $0.00/g
Min. Order
10g
Purity
98.0%
Supply Ability
500kg/month
Release date
2021-07-14
Hebei Mojin Biotechnology Co., Ltd
Product
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE 6564-72-3
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-24
Hebei Guanlang Biotechnology Co., Ltd.
Product
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE 6564-72-3
Price
US $10.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2021-04-28

6564-72-3, 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSERelated Search:

(S)-Valiolamine Voglibose Valiolamine (2S,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylMethoxy)-5-[(phenylMethoxy)Methyl]-cyclohexanone (R)-Valiolamine Voglibose ETHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-THIOGLUCOPYRANOSIDE Methyl-2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE Methyl beta-D-ribofuranoside 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranosyl azide 3,4,6-Triacetate FMOC-SER(GALNAC(AC)3-ALPHA-D)-OH Penta-O-benzoyl-alpha-D-mannopyranose 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-α-D-glucopyranosyl azide 3,4,6-Triacetate FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH D-Galactose 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

  • 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose (for Voglibose)
  • Voglibose int
  • Voglibose Impurity 1
  • 2,3,4,6-Tetra-O-benzyl-D-glycopyranose
  • 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE
  • 2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE
  • 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose
  • benzylglucopyranose
  • 6-Tetra-O-benzyl-D-glucopyranose
  • 2,3,4,6-tetra-o-benzyl-d-glucose
  • 2,3,4,6-Tetra-o-benzyl-D-glucopyransoe
  • 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranose
  • 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE ,GB
  • 2,3,4,6-TETRA-O-ACETYL A-D-GLUCOPYRANOSIDE
  • 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranos
  • alpha-D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylMethyl)-
  • a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylMethyl)-
  • Voglibose TBG IMpurity
  • (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol
  • 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose SynonyMs 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranose
  • 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranose
  • Voglibose TBG impurities
  • Voglibose alpha-TBG Impurity
  • 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose
  • 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOSE 6564-72-3
  • 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE USP/EP/BP
  • 2,3,4,6-TETRA-O-BENZYL-ALPHA GLUCOPYRANOSE（COM）
  • 2,3,4,6-TETRA-O-BENZYL-D-GLUCChemicalbookOPYRANOSE
  • 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(TBG)
  • 2,3,4,6-Tetrakis-O-(phenylmethyl)-α-D-glucopyranose
  • α-D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-
  • Tetrabenzyl glucose
  • 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE
  • 6564-72-3
  • Specialty Synthesis
  • Monosaccharides
  • Monosaccharide
  • O-Substituted Sugars
  • Sugars
  • Carbohydrate Synthesis
  • Carbohydrates
  • Biochemicals and Reagents
  • BioChemical
  • Pharmaceutical Intermediates
  • 6564-72-3