6564-72-3

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE
• Synonyms: 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-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;2,3,4,6-Tetra-O-benzyl-alpha-D-glucose
• CAS NO: 6564-72-3
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.65
• EINECS: 1806241-263-5
• Product Categories: Pharmaceutical Intermediates
• Mol File: 6564-72-3.mol
• Article Data: 180

Chemical Properties

• Melting Point: 151-156 °C
• Boiling Point: 672.378 °C at 760 mmHg
• Flash Point: 360.441 °C
• Appearance: /
• Density: 1.22
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: −20°C
• PKA: 11.87±0.70(Predicted)
• Water Solubility: Soluble in CHCl3. Insoluble in water.
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(6564-72-3)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(6564-72-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 6564-72-3(Hazardous Substances Data)

Usage

Description

2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is a significant D-glucopyranose derivative that plays a crucial role in various chemical and pharmaceutical processes. It is characterized by the presence of four benzyl groups attached to the hydroxyl groups at the 2, 3, 4, and 6 positions, which provide steric hindrance and protect the molecule during reactions. This unique structure makes it a valuable intermediate in the synthesis of complex carbohydrates and related compounds.

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is used as an intermediate in the synthesis of Voglibose and Dapagliflozin, which are important drugs for the treatment of type 2 diabetes. Its role in the synthesis process is crucial for the development of these therapeutic agents.
Used in Organic Chemistry:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is used as a key building block in the preparation of α-glucopyranosyl chloride, a versatile reagent for the synthesis of various 1-C-α-D-glucopyranose derivatives. This allows for the creation of a wide range of complex carbohydrate structures with potential applications in various fields.
Used in Carbohydrate Chemistry:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is used as a protecting group in glucosylations and other carbohydrate-related reactions. The benzyl groups provide steric protection, enabling selective reactions to occur at specific sites on the molecule. This selective reactivity is essential for the synthesis of complex carbohydrate structures with precise control over the product's structure.

InChI:InChI=1/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

Synthetic route

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With sulfuric acid; acetic acid In water for 2h; Reflux;	97%
With hydrogenchloride In water; acetic acid at 85℃; for 7h; Reflux;	63%
With sulfuric acid In methanol; water; acetic acid	41%

(Z)-prop-1'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (139684-64-3) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With hydrogenchloride In methanol; acetone for 0.5h;	94%

methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (104992-64-5) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With calcium carbonate; mercury dichloride In water; acetonitrile for 5h; Heating;	77%

2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (70893-32-2) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With N-Bromosuccinimide; water In acetone at 20℃; for 0.5h; Concentration;	73.3%

(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran (660851-96-7) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With trifluoroacetic acid at 65℃; for 3h;	65%

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside (131531-76-5) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With N-Bromosuccinimide; water In water; acetone at 20℃; for 0.5h; Concentration;	62%

methyl 3β-amino-12α-O-(α-D-glucopyranosyl-1')-deoxycholate + methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside (84799-77-9) → 3β-amino-24-hydroxy-7α,12α-di(1'α-glucosyl)-5β-cholane + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With sulfuric acid In acetic acid	A n/a B 53%

1,2:5,6-di-O-isopropylidene-D-glucofuranoside (582-52-5, 2595-05-3, 10368-86-2, 13100-30-6, 14686-89-6, 23262-79-5, 26597-74-0, 26623-15-4, 38166-58-4, 38166-60-8, 79943-22-9, 83730-28-3) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
(i) HCl, AllOH, (ii) (benzylation), (iii) aq. HCl, acetone; Multistep reaction;

methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside (19488-61-0) → 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + 2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7)

Conditions	Yield
With trifluorormethanesulfonic acid; acetic acid for 4h; Yield given. Yields of byproduct given;
With trifluorormethanesulfonic acid; acetic acid for 240h; Yield given. Yields of byproduct given;

2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With pyridine; dmap In dichloromethane at 22℃; Equilibrium constant;

isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (114967-51-0) → 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + 2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7)

Conditions	Yield
With trifluorormethanesulfonic acid; acetic acid for 3h; Yield given. Yields of byproduct given;

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (115969-49-8) → 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + 2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7)

Conditions	Yield
With trifluorormethanesulfonic acid; acetic acid for 0.5h;

2-benzyloxyethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (82231-40-1) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + 2-benzyloxyethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

Conditions	Yield
With titanium tetrachloride In dichloromethane for 0.00111111h; Ambient temperature; Yield given. Yields of byproduct given;

1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (18685-22-8) → 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3)

Conditions	Yield
With acetic acid

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-D-glucofuranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 18685-22-8 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 139684-64-3 (Z)-prop-1'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 130781-25-8 Phenyl 3,4,6-tri-O-benzyl-1-seleno-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 6586-70-5 isopropyl-(tetra-O-acetyl-β-D-glucopyranoside) 
• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 1338567-47-7 C₃₆H₃₇Cl₃O₆ 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 165680-87-5 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl diethyl phosphite 
• 78880-45-2 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-ethyl-phenoxy)-tetrahydro-pyran 
• 78880-45-2 (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-ethyl-phenoxy)-tetrahydro-pyran 
• 78880-50-9 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-ethoxy-phenoxy)-tetrahydro-pyran 
• 78880-50-9 (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-ethoxy-phenoxy)-tetrahydro-pyran 
• 78880-49-6 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(3-methoxyphenoxy)tetrahydro-2H-pyran 
• 78880-49-6 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(3-methoxyphenoxy)tetrahydro-2H-pyran 
• 98044-35-0 C₃₅H₃₆ClNO₉S 
• 91303-31-0 C₃₄H₃₇O₈P 
• 58781-26-3 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1?1)-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 58781-27-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 25018-28-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 

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