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

Base Information

• Chemical Name: p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 793672-55-6
• Molecular Formula: C₃₄H₃₆O₅S
• Molecular Weight: 556.723
• Mol file: 793672-55-6.mol

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

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

There total 11 articles about p-methylphenyl 3,4,6-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: 97.0%

p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose (634197-71-0) → p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (793672-55-6)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/ol048427o

Reference yield: 50.0%

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) + para-thiocresol (106-45-6) → p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (793672-55-6)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; for 2h; Reflux; Inert atmosphere;

DOI:10.1039/c9cc07194f

Reference yield:

para-thiocresol (106-45-6) → p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (793672-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 97 percent / NaOMe / methanol; CH₂Cl₂ / 2.5 h / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ol048427o

upstream raw materials:

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

para-thiocresol

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

D-glucose pentaacetate

Downstream raw materials:

(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

p-tolyl 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-α(1→2)-3,4,6-tri-O-benzylthio-β-D-glucopyranoside

p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

p-tolyl 2-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside