(2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol
• CAS No.: 6564-72-3
• Molecular Formula: C34H36O6
• Molecular Weight: 540.656
• European Community (EC) Number: 667-304-9,432-870-6
• DSSTox Substance ID: DTXSID701223333
• Nikkaji Number: J348.082H
• Wikidata: Q76421933
• Mol file: 6564-72-3.mol

Synonyms:6564-72-3;(2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol;2,3,4,6-Tetra-O-benzyl-D-glucopyranose;2,3,4,6-TETRA-O-BENZYL-alpha-D-GLUCOPYRANOSE;(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol;MFCD00023849;2,3,4,6-Tetra-O-benzyl-a-D-glucopyranose;MFCD00066004;OGOMAWHSXRDAKZ-RUOAZZEASA-N;2,3,4,6-Tetra-O-benzyl-alpha-glucopyranose;SCHEMBL1457585;DTXSID701223333;AKOS016008732;CS-W011468;AS-14143;F11423;2,3,4,6-tetra-O-benzyl-alpha-D-gluco-pyranose;a-DGlucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)-;2,3,4,6-Tetrakis-O-(phenylmethyl)-alpha-D-glucopyranose;(2S,3R,4S,5R,6R)-3,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-ol

Chemical Property of (2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol

Chemical Property:

• Appearance/Colour: White crystaline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 151-156 °C
• 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
• Water Solubility.: Soluble in CHCl3. Insoluble in water.
• 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:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

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@H](O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• 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.

Technology Process of (2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol

There total 356 articles about (2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol 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:

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

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

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

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

Downstream raw materials:

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

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

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

tetra-O-benzyl glucopyranosyl chloride

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