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

Base Information

• Chemical Name: 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one
• CAS No.: 940285-55-2
• Molecular Formula: C₅₁H₅₉NO₅SSi₂
• Molecular Weight: 854.27
• Mol file: 940285-55-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one 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: 78.0%

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde (940285-45-0) + C25H41O2NSP(1+)*Br(1-) → 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one (940285-55-2)

Guidance literature:

C₂₅H₄₁O₂NSP⁽¹⁺⁾*Br^(1-); With n-butyllithium; In hexane; dichloromethane; at -78 ℃; for 0.25h;

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde; In hexane; dichloromethane; at -78 - 0 ℃; Further stages.;

DOI:10.1021/jo062206+

Reference yield:

C15H19O4NS2 (940285-47-2) → 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one (940285-55-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / mercuric trifluoroacetate; acetic acid / 45 - 55 °C

2.1: 60 percent / aq. NaOH / methanol / 3 h

3.1: 62 percent / CBr₄; Ph₃P / CH₂Cl₂ / 2 h / 0 °C

4.1: 791 mg / benzene / 5 h / 40 °C

5.1: n-BuLi / CH₂Cl₂; hexane / 0.25 h / -78 °C

5.2: 78 percent / CH₂Cl₂; hexane / -78 - 0 °C

With sodium hydroxide; n-butyllithium; carbon tetrabromide; mercury(II) trifluoroacetate; acetic acid; triphenylphosphine; In methanol; hexane; dichloromethane; benzene; 5.2: Wittig reaction;

DOI:10.1021/jo062206+

Reference yield:

3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide (940285-41-6) → 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one (940285-55-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 54 percent / DIBAL-H / toluene / -78 - 0 °C

2.1: n-BuLi / CH₂Cl₂; hexane / 0.25 h / -78 °C

2.2: 78 percent / CH₂Cl₂; hexane / -78 - 0 °C

With n-butyllithium; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; 2.2: Wittig reaction;

DOI:10.1021/jo062206+

upstream raw materials:

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

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

C₁₅H₁₉O₄NS₂

N-(4-methoxybenzyl)-4-acetoxymethyl-5-methyl-thiazol-2-one

Downstream raw materials:

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