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

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
• CAS No.: 4132-28-9
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.656
• Hs Code.: 29400090
• European Community (EC) Number: 609-908-7,432-870-6
• DSSTox Substance ID: DTXSID001232816
• Nikkaji Number: J338.547G
• Wikidata: Q106890823
• Mol file: 4132-28-9.mol

Synonyms:4132-28-9;2,3,4,6-Tetra-O-benzyl-D-glucopyranose;(3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-6-((BENZYLOXY)METHYL)TETRAHYDRO-2H-PYRAN-2-OL;tetrabenzylglucose;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol;D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-;(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol;(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;MFCD00066004;C34H36O6;SCHEMBL1793061;AMY8984;OGOMAWHSXRDAKZ-BKJHVTENSA-N;DTXSID001232816;AC-772;2,3,4,6-tetra-O-benzylglucopyranose;AKOS015896450;CS-W011467;2,3,4,6-tetra-O-benzyl glucopyranose;2,3,4,6-tetra-O-benzyl-glucopyranose;DS-10758;2,3,4,6-terta-O-Benzyl-D-Glucopyranose;A25206;EN300-262955;2-O,3-O,4-O,6-O-Tetrabenzyl-D-glucopyranose;2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose;A1-00201;J-620002;a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)-;2,3,4,6-Tetra-O-benzyl-D-glucopyranose, >=98% (TLC);2,3,4,6-Tetra-O-benzyl-D-glucopyranose, >=98.0% (TLC);3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol

Chemical Property of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Chemical Property:

• Appearance/Colour: White crystaline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 145-149 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 672.378 °C at 760 mmHg
• PKA: 11.87±0.70(Predicted)
• Flash Point: 360.441 °C
• PSA: 66.38000
• Density: 1.222 g/cm³
• LogP: 5.67660
• Storage Temp.: −20°C
• Solubility.: Soluble in chloroform
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 540.25118886
• Heavy Atom Count: 40
• Complexity: 665

Purity/Quality:

≥95% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (cas# 4132-28-9) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

There total 299 articles about 2,3,4,6-Tetra-O-benzyl-D-glucopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

Reference yield: 100.0%

2,3,4,6-tetra-O-benzyl-1-O-propynyl-D-glucopyranoside → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With water; gold(III) chloride; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1021/ja062425c

Reference yield: 100.0%

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid

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

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

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

2-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrimidine

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

2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-bis(2-hydroxy-4,5-methylenedioxyphenyl)-D-glucitol

ethyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate

Refernces

• 1、 Ahuja-Casarín, Ana I.,Merino-Montiel, Penélope,Vega-Baez, José Luis,Montiel-Smith, Sara,Fernandes, Miguel X.,Lagunes, Irene,Maya, Inés,Padrón, José M.,López, óscar,Fernández-Bola?os, José G.. "Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors". . p. 138 - 146. Retrieved 2020/11/27.
• 2、 -. "Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof". Paragraph 0033; 0057; 0062. . Retrieved 2021/04/03.