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

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

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;2,3,4,6-Tetra-O-benz;Voglibose Impurity 4;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

Molecular Weight:: 540.65

MDL Number:: MFCD00023849

MOL File:: 4132-28-9.mol

Last updated:2024-11-18 17:01:59

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

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
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

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P261-P280-P271

Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36-24/25

WGK Germany

HS Code

29400090

NFPA 704

	1
0		0

2,3,4,6-Tetra-O-benzyl-D-glucopyranose price More Price(43)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	86730	2,3,4,6-Tetra-O-benzyl-D-glucopyranose ≥98.0% (TLC)	4132-28-9	1g	$26	2024-03-01	Buy
Sigma-Aldrich	86730	2,3,4,6-Tetra-O-benzyl-D-glucopyranose ≥98.0% (TLC)	4132-28-9	5g	$60.5	2024-03-01	Buy
TCI Chemical	T1914	2,3,4,6-Tetra-O-benzyl-D-glucopyranose >97.0%(HPLC)	4132-28-9	1g	$43	2024-03-01	Buy
TCI Chemical	T1914	2,3,4,6-Tetra-O-benzyl-D-glucopyranose >97.0%(HPLC)	4132-28-9	5g	$117	2024-03-01	Buy
Alfa Aesar	H27888	2,3,4,6-Tetra-O-benzyl-D-glucopyranose, 98+%	4132-28-9	1g	$45.65	2024-03-01	Buy

Product number	Packaging	Price	Buy
86730	1g	$26	Buy
86730	5g	$60.5	Buy
T1914	1g	$43	Buy
T1914	5g	$117	Buy
H27888	1g	$45.65	Buy

2,3,4,6-Tetra-O-benzyl-D-glucopyranose Chemical Properties,Uses,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

Global( 446)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Beijing Ribio Biotech Co.,Ltd	010-62664360 +8613328773880	wucy@ribio.com.cn	China	117	58
Shanghai Worldyang Chemical Co.,Ltd.	+86-021-56795779 +8613651600618	sales@worldyachem.com	China	1073	58
Shanghai Yingrui Biopharma Co.,Ltd	21-33585366	export01@shyrchem.com	CHINA	1319	58
Shanghai Jinli Pharmaceutical Co.,Ltd	+86-21-57256005 +86-15921811235	chang@shjlchem.com	China	20	58
Xinxiang Aurora Biotechnology Co.,Ltd.	+86-0086-0373-3088722 +8618637352520	info@aurora-biotech.com	China	93	58
Hebei Weibang Biotechnology Co., Ltd	+8615531157085	abby@weibangbio.com	China	8812	58
Hebei Mojin Biotechnology Co., Ltd	+86 13288715578 +8613288715578	sales@hbmojin.com	China	12840	58
Hebei Mojin Biotechnology Co.,Ltd	+86-15028179902	angelia@hbmojin.com	China	1177	58
Frapp's ChemicalNFTZ Co., Ltd.	+86 (576) 8169-6106	sales@frappschem.com	China	880	50
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29791	60

Supplier	Advantage
Beijing Ribio Biotech Co.,Ltd	58
Shanghai Worldyang Chemical Co.,Ltd.	58
Shanghai Yingrui Biopharma Co.,Ltd	58
Shanghai Jinli Pharmaceutical Co.,Ltd	58
Xinxiang Aurora Biotechnology Co.,Ltd.	58
Hebei Weibang Biotechnology Co., Ltd	58
Hebei Mojin Biotechnology Co., Ltd	58
Hebei Mojin Biotechnology Co.,Ltd	58
Frapp's ChemicalNFTZ Co., Ltd.	50
Capot Chemical Co.,Ltd.	60

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-21	2,3,4,6-Tetra-O-Benzyl-D-Glucopyranose 4132-28-9	US $0.00 / Kg	1Kg	98%	20Ton	Xinxiang Aurora Biotechnology Co.,Ltd.
2024-11-21	2,3,4,6-Tetra-O-benzyl-D-glucopyranose 4132-28-9	US $0.00 / kg	1kg	98%min	10000kg	WUHAN FORTUNA CHEMICAL CO., LTD
2024-11-18	2,3,4,6-Tetra-O-benzyl-D-glucopyranose 4132-28-9	US $10.00 / kg	1kg	99%	100 mt	Hebei Weibang Biotechnology Co., Ltd

2,3,4,6-Tetra-O-Benzyl-D-Glucopyranose
4132-28-9
US $0.00 / Kg
98%
Xinxiang Aurora Biotechnology Co.,Ltd.

2,3,4,6-Tetra-O-benzyl-D-glucopyranose
4132-28-9
US $0.00 / kg
98%min
WUHAN FORTUNA CHEMICAL CO., LTD

2,3,4,6-Tetra-O-benzyl-D-glucopyranose
4132-28-9
US $10.00 / kg
99%
Hebei Weibang Biotechnology Co., Ltd

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

2,3,4,6-Tetra-O-benzyl-D-glucopyranose(4132-28-9)FT-IR

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2,3,4,6-Tetra-O-benzyl-D-glucopyranose(for Voglibose) 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 Voglibose Impurity 4 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 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 (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 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