(3,4,5-Tribenzoyloxy-6-prop-2-enyloxan-2-yl)methyl benzoate

Base Information

• Chemical Name: (3,4,5-Tribenzoyloxy-6-prop-2-enyloxan-2-yl)methyl benzoate
• CAS No.: 98854-01-4
• Molecular Formula: C₃₇H₃₂O₉
• Molecular Weight: 620.656
• DSSTox Substance ID: DTXSID60913041
• Mol file: 98854-01-4.mol

Synonyms:3-(tetra-O-benzoyl-alpha-glucopyranosyl)-1-propene;tetrabenzoyl-Glu-propene

Chemical Property of (3,4,5-Tribenzoyloxy-6-prop-2-enyloxan-2-yl)methyl benzoate

Chemical Property:

• Vapor Pressure: 4.77E-21mmHg at 25°C
• Boiling Point: 728°Cat760mmHg
• Flash Point: 299.8°C
• PSA: 114.43000
• Density: 1.3g/cm³
• LogP: 5.86370
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 15
• Exact Mass: 620.20463259
• Heavy Atom Count: 46
• Complexity: 1020

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1C(C(C(C(O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5

Technology Process of (3,4,5-Tribenzoyloxy-6-prop-2-enyloxan-2-yl)methyl benzoate

There total 5 articles about (3,4,5-Tribenzoyloxy-6-prop-2-enyloxan-2-yl)methyl benzoate 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: 2.3%

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose (22415-91-4) + allyl-trimethyl-silane (762-72-1) → 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1-propene (98920-47-9) + 3-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene (98854-01-4)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 80 ℃;

DOI:10.1016/0008-6215(89)85066-9

Reference yield:

allyltributylstanane (24850-33-7) + 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose (869384-37-2) → 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1-propene (98920-47-9) + 3-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene (98854-01-4)

Guidance literature:

1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 ℃; Inert atmosphere;

allyltributylstanane; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol801710s

Reference yield:

1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose (869384-37-2) + allyl-trimethyl-silane (762-72-1) → 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1-propene (98920-47-9) + 3-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene (98854-01-4)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol801710s

upstream raw materials:

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose

allyl-trimethyl-silane

formyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

allyltributylstanane

Downstream raw materials:

trans-3-(tetra-O-benzoyl-α-D-glucopyranosyl)-1-(p-tolylsulfonyl)-1-propene