phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside
• CAS No.: 1352406-97-3
• Molecular Formula: C₃₀H₃₂O₉S₂
• Molecular Weight: 600.711
• Mol file: 1352406-97-3.mol

Synonyms:phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside

There total 7 articles about phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-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: 95.0%

phenyl 3-O-methyl-4,6-O-benzylidene-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside (1352406-94-0) + acetic anhydride (108-24-7) → phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside (1352406-97-3)

Guidance literature:

With pyridine; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

phenyl 4,6-O-benzylidene-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside (1352406-92-8) → phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside (1352406-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: ozone / dichloromethane / 0.05 h / -78 °C

2: sodium tetrahydroborate / ethanol / 20 h / 0 - 20 °C / Inert atmosphere

3: pyridine / 72 h / 20 °C / Inert atmosphere

4: pyridine / 22 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; ozone; In ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

phenyl 2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside (1352406-91-7) → phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside (1352406-97-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium methylate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: IR-120 H⁺ resin / 0.75 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3 h / 70 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.05 h / -78 °C

4.1: sodium tetrahydroborate / ethanol / 20 h / 0 - 20 °C / Inert atmosphere

5.1: pyridine / 72 h / 20 °C / Inert atmosphere

6.1: pyridine / 22 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; ozone; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.10.005

upstream raw materials:

phenyl 2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside

phenyl 4,6-O-benzylidene-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside

phenyl 4,6-O-benzylidene-3-O-methyl-5-C-hydroxymethyl-1-thio-β-D-glucopyranoside

phenyl 3-O-methyl-4,6-O-benzylidene-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside

Downstream raw materials:

1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

1'-(2'-O-acetyl-4',6'-O-benzylidene-3'-O-methyl-5'-C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine