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

Base Information

• Chemical Name: 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde
• CAS No.: 940285-45-0
• Molecular Formula: C₃₈H₄₆O₄Si₂
• Molecular Weight: 622.952
• Mol file: 940285-45-0.mol

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

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

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 carbaldehyde

There total 6 articles about 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde 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: 54.0%

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide (940285-41-6) → 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde (940285-45-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 - 0 ℃;

DOI:10.1021/jo062206+

Reference yield:

1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose (940285-39-2) → 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde (940285-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / toluene / 12 h / 0 °C

2: 54 percent / DIBAL-H / toluene / -78 - 0 °C

With diisobutylaluminium hydride; In toluene;

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 carbaldehyde (940285-45-0)

Guidance literature:

Multi-step reaction with 6 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

6: 54 percent / DIBAL-H / toluene / -78 - 0 °C

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

DOI:10.1021/jo062206+

upstream raw materials:

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

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

D-2-deoxyribose

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

Downstream raw materials:

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