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

Name
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE
EINECS 667-304-9
CAS No. 6564-72-3
Article Data169
CAS DataBase
Density 1.222 g/cm³
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
Appearance White crystaline solid
Safety 22-24/25
Risk Codes R36/37/38
Molecular Structure
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;
PSA 66.38000
LogP 5.67660

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

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%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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 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

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

...Expand

: 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

Conditions	Yield
(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

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;

...Expand

: 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

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

: 114967-51-0
isopropyl 2,3,4,6-tetra-O-benzyl-β-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

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

...Expand

: 115969-49-8
2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-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

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

...Expand

: 82231-40-1
2-benzyloxyethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

A: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

B: 2-benzyloxyethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

Conditions

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

: 18685-22-8
1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

Conditions

Conditions	Yield
With acetic acid

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

Product Name

2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE

Synthetic route

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

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