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

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.

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

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 50-99-7 D-glucose 
• 100-39-0 benzyl bromide 
• 660851-94-5 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran-4-yl ester 
• 18685-22-8 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 186038-72-2 N-phthalyl-L-cysteine benzyl ester 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 660852-03-9 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran-4-yl ester 
• 866719-67-7 C₂₉H₂₄Cl₃NO₉ 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 78184-86-8 1,3,4,5-tetra-O-benzyl-α-L-sorbopyranoside 
• 80726-93-8 2,3,4,6-Tetra-O-benzyl-D-glucosehydrazon 
• 58781-27-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 124064-68-2 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl (phenylsulfate) 
• 124040-40-0 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl (phenylsulfate) 
• 86496-30-2 (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime 
• 14233-48-8 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 82110-04-1 (E)-2,4,6-tri-O-benzyl-2-dehydro-3-deoxy-D-erythro-hex-2-enitol 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride 
• 82064-64-0 (Z)-2,4,6-tri-O-benzyl-2-dehydro-3-deoxy-D-erythro-hex-2-enitol 
• 16134-31-9 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enopyranose 
• 132201-25-3 (2Z,4S,5R)-2,4-6-tris(benzyloxy)-5-hydroxyhex-2-enal 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.