p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside
• CAS No.: 762287-64-9
• Molecular Formula: C₃₄H₃₀O₈S
• Molecular Weight: 598.673
• DSSTox Substance ID: DTXSID001176999
• Nikkaji Number: J2.707.936I
• Mol file: 762287-64-9.mol

Synonyms:DTXSID001176999;762287-64-9;p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside;beta-D-Glucopyranoside, 4-methylphenyl 1-thio-, 2,3,4-tribenzoate;4-Methylphenyl 2-O,3-O,4-O-tribenzoyl-1-thio-beta-D-glucopyranoside

Chemical Property of p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside

Chemical Property:

• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 598.16613908
• Heavy Atom Count: 43
• Complexity: 902

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)SC2C(C(C(C(O2)CO)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: CC1=CC=C(C=C1)S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5

Technology Process of p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside

There total 10 articles about p-Tolyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside 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%

p-methylphenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside (807360-79-8) → S-4-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (762287-64-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 4h; pH=6;

DOI:10.1002/anie.200460176

Reference yield: 91.1%

p-methylphenyl 2,3,4-tri-O-benzoyl-6-O-trityl-1-thio-β-D-glucopyranoside (762287-69-4) → S-4-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (762287-64-9)

Guidance literature:

With iron(III) chloride hexahydrate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo9000993

Reference yield: 89.0%

p-tolyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside → S-4-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (762287-64-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 25 ℃; for 4h; pH=6;

DOI:10.1021/acs.orglett.7b01242

upstream raw materials:

p-methylphenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

p-methylphenyl 2,3,4-tri-O-benzoyl-6-O-trityl-1-thio-β-D-glucopyranoside

D-glucose pentaacetate

p-methylphenyl 1-thio-β-D-glucopyranoside