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

Base Information

• Chemical Name: p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 1363157-76-9
• Molecular Formula: C₄₁H₄₀O₆S
• Molecular Weight: 660.831
• Mol file: 1363157-76-9.mol

Synonyms:p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

There total 4 articles about p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-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: 86.0%

benzoyl chloride (98-88-4) + ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol (479252-05-6) → p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (1363157-76-9)

Guidance literature:

With pyridine; at 20 ℃; for 4h;

DOI:10.1002/ejoc.201900815

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (1363157-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; pyridine / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

2.2: 0 - 20 °C

3.1: camphor sulfonic acid / dichloromethane; methanol / 20 °C

4.1: pyridine / 0 - 20 °C

With pyridine; dmap; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2017.05.012

Reference yield:

β-1-p-tolylthio-6-O-trityl-D-glucopyranose (819814-42-1) → p-methylphenyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (1363157-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

1.2: 0 - 20 °C

2.1: camphor sulfonic acid / dichloromethane; methanol / 20 °C

3.1: pyridine / 0 - 20 °C

With pyridine; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2017.05.012

upstream raw materials:

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

β-1-p-tolylthio-6-O-trityl-D-glucopyranose

p-tolyl-2,3,4-tri-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside

benzoyl chloride

Downstream raw materials:

methyl 6-O-(6'-O-benzoyl-2',3',4'-tri-O-benzyl-α-β-d-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-benzoyl-D-glucopyranosyl-α-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside