4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS No.: 496810-91-4
• Molecular Formula: C₆₇H₅₃BrO₁₇S
• Molecular Weight: 1242.12
• Mol file: 496810-91-4.mol

Synonyms:4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property of 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

There total 4 articles about 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-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: 70.0%

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (105376-04-3,138661-53-7,113214-71-4) + 4-bromophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (496810-90-3) → 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (496810-91-4)

Guidance literature:

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside; 4-bromophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside; With 4 A molecular sieve; In dichloromethane; for 1h;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; for 4h;

DOI:10.1139/v02-101

Reference yield:

4-bromophenyl 1-thio-β-D-glucopyranoside (95840-17-8) → 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (496810-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 4-dimethylaminopyridine / pyridine; CHCl₃; methanol / 20 °C

2.1: 1.34 g / various solvents

3.1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h

4.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h

4.2: 70 percent / dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂ / 4 h

With dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; In pyridine; methanol; dichloromethane; chloroform; various solvents;

DOI:10.1139/v02-101

Reference yield:

(2S,3R,4S,5S,6R)-2-(4-Bromo-phenylsulfanyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol → 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (496810-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1.34 g / various solvents

2.1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h

3.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h

3.2: 70 percent / dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂ / 4 h

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; various solvents;

DOI:10.1139/v02-101

upstream raw materials:

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

4-bromophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

4-bromophenyl 1-thio-β-D-glucopyranoside

4-bromophenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside