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
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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)
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Safety

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

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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
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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

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

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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
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