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

Base Information

• Chemical Name: 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide
• CAS No.: 940285-41-6
• Molecular Formula: C₃₈H₄₅NO₃Si₂
• Molecular Weight: 619.951
• Mol file: 940285-41-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide 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: 53.0%

1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose (940285-39-2) + diethylaluminium cyanide (5804-85-3) → 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide (940285-41-6) + 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-β-D-ribofuranosyl cyanide (940285-42-7)

Guidance literature:

In toluene; at 0 ℃; for 12h;

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) → 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide (940285-41-6)

Guidance literature:

Multi-step reaction with 5 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

5: 53 percent / toluene / 12 h / 0 °C

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

DOI:10.1021/jo062206+

Reference yield:

3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-D-ribofuranose → 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide (940285-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

2: 53 percent / toluene / 12 h / 0 °C

With triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo062206+

upstream raw materials:

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

diethylaluminium cyanide

D-2-deoxyribose

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

Downstream raw materials:

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)-E-vinyl]-5-methyl-thiazol-2-one

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

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