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2,3,4,6-Tetra-O-benzyl-alpha-D-glucose
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Name

2,3,4,6-Tetra-O-benzyl-alpha-D-glucose

 EINECS 667-304-9
CAS No. 6564-72-3 Density 1.222 g/cm3
PSA 66.38000 LogP 5.67660
Solubility Soluble in CHCl3. Insoluble in water. Melting Point 151-156 °C
Formula C34H36O6 Boiling Point 672.378 °C at 760 mmHg
Molecular Weight 540.656 Flash Point 360.441 °C
Transport Information N/A Appearance White crystaline solid
Safety 22-24/25 Risk Codes R36/37/38
Molecular Structure Molecular Structure of 6564-72-3 (2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE) Hazard Symbols Xi
Synonyms

Glucopyranose,2,3,4,6-tetra-O-benzyl-, a-D- (8CI);2,3,4,6-Tetra-O-benzyl-alpha-D-glucose;2,3,4,6-tetra-O-benzyl-d-glucopyranose;

Article Data 169

2,3,4,6-Tetra-O-benzyl-alpha-D-glucose Synthetic route

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

6564-72-3

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

Conditions
ConditionsYield
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 acid41%
139684-64-3

(Z)-prop-1'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

6564-72-3

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

Conditions
ConditionsYield
With hydrogenchloride In methanol; acetone for 0.5h;94%
104992-64-5

methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

6564-72-3

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

Conditions
ConditionsYield
With calcium carbonate; mercury dichloride In water; acetonitrile for 5h; Heating;77%
70893-32-2

2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

6564-72-3

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

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetone at 20℃; for 0.5h; Concentration;73.3%
660851-96-7

(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran

6564-72-3

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

Conditions
ConditionsYield
With trifluoroacetic acid at 65℃; for 3h;65%
131531-76-5

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside

6564-72-3

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

Conditions
ConditionsYield
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 3β-amino-12α-O-(α-D-glucopyranosyl-1')-deoxycholate

84799-77-9

methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

A

3β-amino-24-hydroxy-7α,12α-di(1'α-glucosyl)-5β-cholane

3β-amino-24-hydroxy-7α,12α-di(1'α-glucosyl)-5β-cholane

B

6564-72-3

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

Conditions
ConditionsYield
With sulfuric acid In acetic acidA n/a
B 53%
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

1,2:5,6-di-O-isopropylidene-D-glucofuranoside

6564-72-3

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

Conditions
ConditionsYield
(i) HCl, AllOH, (ii) (benzylation), (iii) aq. HCl, acetone; Multistep reaction;
19488-61-0

methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside

A

80300-30-7

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

B

6564-72-3

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

C

59531-24-7

2,3,4,6-tetra-O-benzyl-D-glucopyranoside

Conditions
ConditionsYield
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;
59531-24-7

2,3,4,6-tetra-O-benzyl-D-glucopyranoside

6564-72-3

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

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

2,3,4,6-Tetra-O-benzyl-alpha-D-glucose Specification

The CAS register number of a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)- is 6564-72-3. It also can be called as Glucopyranose,2,3,4,6-tetra-O-benzyl-, a-D- (8CI) and the systematic name about this chemical is 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The molecular formula about this chemical is C34H36O6 and the molecular weight is 540.65. It belongs to the following product categories which include Pharmaceutical Intermediates and so on.

Physical properties about a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)- are: (1)ACD/LogP: 6.00; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 9; (4)ACD/LogD (pH 7.4): 9; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 2005989; (8)ACD/KOC (pH 7.4): 2005921; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 66.38 Å2; (13)Index of Refraction: 1.619; (14)Molar Refractivity: 155.285 cm3; (15)Molar Volume: 442.429 cm3; (16)Polarizability: 61.56x10-24cm3; (17)Surface Tension: 55.009 dyne/cm; (18)Density: 1.222 g/cm3; (19)Flash Point: 360.441 °C; (20)Enthalpy of Vaporization: 103.758 kJ/mol; (21)Boiling Point: 672.378 °C at 760 mmHg.

Preparation: this chemical can be prepared by benzyl-(tetra-O-benzyl-b-D-glucopyranoside). This reaction will need reagent of ammonium formate and solvent of methanol. This reaction needs catalytic agent of 10percent Pd/Al2O3. The reaction time is 12 hours. The yield is about 75%.

Uses of a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)-: it can be used to produce benzoic acid 3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester with benzoic acid. This reaction will need reagent of Ph3P (TPP), diisopropyl azodicarboxylate (DIAD) and solvent of tetrahydrofuran. The reaction time is 2 hours with reaction temperature of -50 - 20 °C. The yield is about 54%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is toxic in contact with skin. It is also toxic if swallowed. If you want to store this chemical, keep in a cool place.

You can still convert the following datas into molecular structure:
(1)SMILES: O(Cc1ccccc1)[C@@H]4[C@@H](OCc2ccccc2)[C@H](OCc3ccccc3)[C@H](OC4O)COCc5ccccc5
(2)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
(3)InChIKey: OGOMAWHSXRDAKZ-BKJHVTENBB
(4)Std. 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
(5)Std. InChIKey: OGOMAWHSXRDAKZ-BKJHVTENSA-N

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