1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine

Base Information

• Chemical Name: 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine
• CAS No.: 153709-57-0
• Molecular Formula: C₁₉H₂₀N₂O₇
• Molecular Weight: 388.377
• Mol file: 153709-57-0.mol

Synonyms:1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine

Chemical Property of 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine

There total 4 articles about 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)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: 87.0%

1-<3-O-benzyl-5,6-O-carbonyl-2-O-(phenoxythiocarbonyl)-beta-D-glucofuranosyl>thymine (153709-61-6) → 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine (153709-57-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 - 90 ℃; for 1h;

DOI:10.1080/07328319308018561

Reference yield:

2,4-dihydroxy-5-methylpyrimidine (65-71-4,80289-22-1) → 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine (153709-57-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,2-dichloro-ethane / 65 - 70 °C

2: 87 percent / 99 percent stannic chloride / 1,2-dichloro-ethane / 12 h / Heating

3: 1.) acetyl chloride, 2.) triethylamine / 1.) 1,4-dioxane, methanol, reflux, 24 h, 2.) dichloromethane, 4 h

4: 87 percent / 97 percent tributyltin hydride, AIBN / toluene / 1 h / 85 - 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tin(IV) chloride; triethylamine; acetyl chloride; In 1,2-dichloro-ethane; toluene;

DOI:10.1080/07328319308018561

Reference yield:

1-(2-O-acetyl-3-O-benzyl-5,6-O-carbonyl-beta-D-glucofuranosyl)thymine (153709-53-6) → 1-(3-O-benzyl-5,6-O-carbonyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymine (153709-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) acetyl chloride, 2.) triethylamine / 1.) 1,4-dioxane, methanol, reflux, 24 h, 2.) dichloromethane, 4 h

2: 87 percent / 97 percent tributyltin hydride, AIBN / toluene / 1 h / 85 - 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; acetyl chloride; In toluene;

DOI:10.1080/07328319308018561

upstream raw materials:

1-<3-O-benzyl-5,6-O-carbonyl-2-O-(phenoxythiocarbonyl)-beta-D-glucofuranosyl>thymine

2,4-dihydroxy-5-methylpyrimidine

1-(2-O-acetyl-3-O-benzyl-5,6-O-carbonyl-beta-D-glucofuranosyl)thymine

2,4-bis(trimethylsiloxy)-5-methylpyrimidine