ChemicalBook > CAS DataBase List > 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

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
More
Less

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)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
HS Code 
29400090
More
Less

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.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
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
Sigma-Aldrich
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
TCI Chemical
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
TCI Chemical
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
Alfa Aesar
Product number
H27888
Product name
2,3,4,6-Tetra-O-benzyl-D-glucopyranose, 98+%
Packaging
1g
Price
$45.65
Updated
2024/03/01
More
Less

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

More
Less

2,3,4,6-Tetra-O-benzyl-D-glucopyranose Suppliers

Canada 1 China 358 Czech 1 Germany 7 India 22 Japan 2 Slovakia 1 Switzerland 5 United Kingdom 14 United States 35 Global 446
MDP ChemControl Ltd.
Tel
--
Fax
--
Email
chemcontrol@nextra.sk
Country
Slovakia
ProdList
6700
Advantage
60
More
Less

View Lastest Price from 2,3,4,6-Tetra-O-benzyl-D-glucopyranose manufacturers

Xinxiang Aurora Biotechnology Co.,Ltd.
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
Hebei Weibang Biotechnology Co., Ltd
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
Hebei Mojin Biotechnology Co.,Ltd
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

4132-28-9, 2,3,4,6-Tetra-O-benzyl-D-glucopyranoseRelated Search:

Tetrahydropyran Centchroman Benzyl benzoate BENZYL GLYCIDYL ETHER Benzyltrimethylammonium chloride N,N-Dimethylbenzylamine 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Dibenzylideneacetone Benzyl chloride Benzyl alcohol Benzyltriethylammonium chloride Benzyl bromide DEXTROSE 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE (R)-Valiolamine Voglibose (2S,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylMethoxy)-5-[(phenylMethoxy)Methyl]-cyclohexanone Valiolamine (S)-Valiolamine Voglibose

  • 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(for Voglibose)
  • Voglibose Impurity 4
  • 2,3,4, 6-4-o-benzyl-d-pyranoglucose
  • 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE , MIXTURE OF ANOMERS
  • 3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)
  • 3,4,5-TRIS(BENZYLOXY)-6-[(BENZYLOXY)METHYL]OXAN-2-OL
  • (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol
  • 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%
  • 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose
  • 2,3,4,6-Tetra-O-benz
  • Tetra-O-benzyl-D-glucopyranose
  • benzyl-D-glucopyranose
  • (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol
  • ucopyranose
  • Tetra-O-Benzyl-D-Glucopyranose(2,3,4,6-Tetra-O-benzyl-D-glucopyranose)
  • 2,3,4,6-Tetra-O-benzyl-D-glucopyranose ISO 9001：2015 REACH
  • 2,3,4,6-Tetra-O-benzyl-O-glucopyranose
  • (3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
  • Garlic oil 8000-78-0
  • Voglibose Intermediates
  • 2,3,4,6-Tetrabenzyl-D-Glucopyranose
  • 2,3,4,6-Tetra-O-benzyl-D-glucopyranose,NA
  • 2,3,4,6-Tetra -0- benzyl- α -D- gluco pyranose
  • 2,3,4,6-Tetrakis-O-benzyl-D-glucopyranose
  • 4132-28-9
  • 4132-28-9 6564-72-3
  • 4231-28-9
  • Halogenated Heterocycles ,Pyrazoles
  • Biochemistry
  • Glucose
  • O-Substituted Sugars
  • Sugars
  • aldehydes
  • Carbohydrates & Derivatives
  • Carbohydrate Synthesis
  • Monosaccharides
  • Specialty Synthesis
  • Carbohydrates
  • Carbohydrates A to
  • Carbohydrates P-ZBiochemicals and Reagents
  • Monosaccharide
  • 13C & 2H Sugars
  • Glycon Biochem