1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose

Base Information

• Chemical Name: 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose
• CAS No.: 940285-39-2
• Molecular Formula: C₃₉H₄₈O₅Si₂
• Molecular Weight: 652.978
• Mol file: 940285-39-2.mol

Synonyms:1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose

Chemical Property of 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose

There total 4 articles about 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose 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: 89.0%

acetic anhydride (108-24-7) + 3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-D-ribofuranose → 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose (940285-39-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo062206+

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose (940285-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / aq. Br₂ / 72 h

2: imidazole / dimethylformamide / 12 h

3: DIBAL-H / diethyl ether / 5 h / -78 °C

4: 89 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; bromine; diisobutylaluminium hydride; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo062206+

Reference yield:

2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone (175020-66-3) → 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose (940285-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / diethyl ether / 5 h / -78 °C

2: 89 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

With diisobutylaluminium hydride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/jo062206+

upstream raw materials:

acetic anhydride

D-2-deoxyribose

2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone

2-deoxy-D-ribonolactone

Downstream raw materials:

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-β-D-ribofuranosyl cyanide

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde

4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one