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

Base Information

Chemical Name:4-[2-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl)-E-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one
CAS No.:940285-52-9
Molecular Formula:C₃₁H₅₁NO₅SSi₂
Molecular Weight:605.987
Hs Code.:

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

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

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

There total 11 articles about 4-[2-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl)-E-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: 40.0%

: 940285-46-1
3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl carbaldehyde

: C₂₅H₄₁O₂NSP⁽¹⁺⁾*Br^(1-)

: 940285-52-9
4-[2-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl)-E-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one

Guidance literature:: C₂₅H₄₁O₂NSP⁽¹⁺⁾*Br^(1-); With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 6h; Further stages.;
DOI:10.1021/jo062206+

Reference yield:

: 940285-47-2
C₁₅H₁₉O₄NS₂

: 940285-52-9
4-[2-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl)-E-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one

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 / tetrahydrofuran; hexane / 0.08 h / -78 °C

5.2: 40 percent / tetrahydrofuran; hexane / 6 h / -78 °C

With sodium hydroxide; n-butyllithium; carbon tetrabromide; mercury(II) trifluoroacetate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 5.2: Wittig reaction;
DOI:10.1021/jo062206+

Reference yield:

: 940285-48-3
N-(4-methoxybenzyl)-4-acetoxymethyl-5-methyl-thiazol-2-one

: 940285-52-9
4-[2-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl)-E-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60 percent / aq. NaOH / methanol / 3 h

2.1: 62 percent / CBr₄; Ph₃P / CH₂Cl₂ / 2 h / 0 °C

3.1: 791 mg / benzene / 5 h / 40 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

4.2: 40 percent / tetrahydrofuran; hexane / 6 h / -78 °C

With sodium hydroxide; n-butyllithium; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 4.2: Wittig reaction;
DOI:10.1021/jo062206+