N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine
• CAS No.: 404870-23-1
• Molecular Formula: C₂₉H₄₃F₂N₃O₄SSi₂
• Molecular Weight: 623.912

Synonyms:N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

Chemical Property of N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

There total 5 articles about N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine 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:

3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-difluoromethylene-tetrahydro-thiophene 1-oxide → N4-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine (404870-23-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 ℃; for 1h;

DOI:10.1021/ol017112v

Reference yield:

1,4-anhydro-2-deoxy-2-C-difluoromethylene-4-thio-D-erythro-pentitol (404870-15-1) → N4-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine (404870-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: mCPBA / CH₂Cl₂ / 1 h / -78 °C

3: TMSOTf / 1,2-dichloro-ethane / 1 h / 50 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ol017112v

Reference yield:

(4S,5R)-4-Benzyloxy-5-benzyloxymethyl-dihydro-thiophen-3-one → N4-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine (404870-23-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 47 percent / Zn dust; HMPT / tetrahydrofuran / 1 h / Heating

2: 92 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 °C

3: 98 percent / NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

4: mCPBA / CH₂Cl₂ / 1 h / -78 °C

5: TMSOTf / 1,2-dichloro-ethane / 1 h / 50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; trimethylsilyl trifluoromethanesulfonate; boron tribromide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ol017112v

upstream raw materials:

1,4-anhydro-2-deoxy-2-C-difluoromethylene-4-thio-D-erythro-pentitol

1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

1,4-anhydro-2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

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