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

Base Information

• Chemical Name: 1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine
• CAS No.: 1352406-99-5
• Molecular Formula: C₂₂H₂₈N₂O₁₁S
• Molecular Weight: 528.537
• Mol file: 1352406-99-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine 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:

phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(tosyloxy)methyl]-1-thio-β-D-glucopyranoside (1352406-97-3) + 2,4-di-O-trimethylsilylthymine (68027-40-7) → 1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-99-5) + 1'-(2'-O-acetyl-4',6'-O-benzylidene-3'-O-methyl-5'-C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-98-4)

Guidance literature:

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 27.5h; Inert atmosphere;

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) → 1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-99-5) + 1'-(2'-O-acetyl-4',6'-O-benzylidene-3'-O-methyl-5'-C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-98-4)

Guidance literature:

Multi-step reaction with 7 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

7.1: N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 27.5 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; ozone; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 7.1: Vorbrüggen coupling;

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) → 1'-(2'-O-acetyl-3'-O-methyl-5'C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-99-5) + 1'-(2'-O-acetyl-4',6'-O-benzylidene-3'-O-methyl-5'-C-[1'-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine (1352406-98-4)

Guidance literature:

Multi-step reaction with 5 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

5: N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 27.5 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; ozone; In ethanol; dichloromethane; 5: Vorbrüggen coupling;

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