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

Base Information

• Chemical Name: 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-E-vinyl]-5-methyl-thiazol-2-one
• CAS No.: 940285-57-4
• Molecular Formula: C₄₃H₅₁NO₄SSi₂
• Molecular Weight: 734.119

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

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

Chemical Property:

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

There total 14 articles about 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-E-vinyl]-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:

4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-5-methyl-thiazol-2-one (940285-56-3) → 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-E-vinyl]-5-methyl-thiazol-2-one (940285-57-4)

Guidance literature:

With iodine; sodium hydrogencarbonate; In benzene; at 20 ℃; for 6h; Irradiation;

DOI:10.1021/jo062206+

Reference yield:

C15H19O4NS2 (940285-47-2) → 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-E-vinyl]-5-methyl-thiazol-2-one (940285-57-4)

Guidance literature:

Multi-step reaction with 7 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

6.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -78 °C

6.2: O₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

6.3: 50 percent / dimethyl sulfide; acetic acid / tetrahydrofuran; pentane / -78 - 20 °C

7.1: 215 mg / NaHCO₃; I₂ / benzene / 6 h / 20 °C / Irradiation

With sodium hydroxide; n-butyllithium; carbon tetrabromide; iodine; tert.-butyl lithium; mercury(II) trifluoroacetate; sodium hydrogencarbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; pentane; 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)-E-vinyl]-5-methyl-thiazol-2-one (940285-57-4)

Guidance literature:

Multi-step reaction with 4 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

3.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: O₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.3: 50 percent / dimethyl sulfide; acetic acid / tetrahydrofuran; pentane / -78 - 20 °C

4.1: 215 mg / NaHCO₃; I₂ / benzene / 6 h / 20 °C / Irradiation

With n-butyllithium; iodine; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; toluene; pentane; benzene; 2.2: Wittig reaction;

DOI:10.1021/jo062206+

upstream raw materials:

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

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

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

C₁₅H₁₉O₄NS₂

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