methyl 2,3-di-O-benzoyl-4-O-[(4-methylphenyl)sulfonyl]-6-O-tritylhexopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzoyl-4-O-[(4-methylphenyl)sulfonyl]-6-O-tritylhexopyranoside
• CAS No.: 20231-37-2
• Molecular Formula: C47H42O10S
• Molecular Weight: 798.8954
• NSC Number: 170240
• DSSTox Substance ID: DTXSID20305327
• Mol file: 20231-37-2.mol

Synonyms:NSC170240;20231-37-2;DTXSID20305327;NSC-170240

Chemical Property of methyl 2,3-di-O-benzoyl-4-O-[(4-methylphenyl)sulfonyl]-6-O-tritylhexopyranoside

Chemical Property:

• Vapor Pressure: 1.23E-29mmHg at 25°C
• Boiling Point: 856°C at 760 mmHg
• Flash Point: 471.5°C
• Density: 1.34g/cm³
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 16
• Exact Mass: 798.24986871
• Heavy Atom Count: 58
• Complexity: 1330

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2C(OC(C(C2OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC)COC(C5=CC=CC=C5)(C6=CC=CC=C6)C7=CC=CC=C7

Technology Process of methyl 2,3-di-O-benzoyl-4-O-[(4-methylphenyl)sulfonyl]-6-O-tritylhexopyranoside

There total 1 articles about methyl 2,3-di-O-benzoyl-4-O-[(4-methylphenyl)sulfonyl]-6-O-tritylhexopyranoside 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:

trityl chloride (76-83-5) + methyl 2,3-di-O-benzoyl-α-D-glucopyranoside (4137-35-3,23397-67-3,102518-21-8,109681-62-1,117124-69-3,149035-49-4) → methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside (20231-37-2)

Guidance literature:

With pyridine; anschliessend Erwaermen mit Toluol-4-sulfonylchlorid;

DOI:10.1039/jr9530000992 DOI:10.1039/jr9580002511 DOI:10.1039/jr9350000685

Reference yield: 96.0%

methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside (20231-37-2) → methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (19488-44-9)

Guidance literature:

With methanol; boron trifluoride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86679-5

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside (20231-37-2) → methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6893-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / BF₃, CH₃OH / CH₂Cl₂ / 2 h / Ambient temperature

2: 84 percent / CBr₄, Ph₃P / acetonitrile / Ambient temperature

3: 89 percent / H₂ / Raney-Nickel / methanol; ethyl acetate

With methanol; carbon tetrabromide; boron trifluoride; hydrogen; triphenylphosphine; nickel; In methanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)86679-5

upstream raw materials:

trityl chloride

methyl 2,3-di-O-benzoyl-α-D-glucopyranoside

Downstream raw materials:

methyl-[O⁴-(toluene-4-sulfonyl)-O⁶-trityl-α-D-glucopyranoside]

Triphenylmethylethylether

methyl-[O⁴-(toluene-4-sulfonyl)-α-D-glucopyranoside]

methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside