N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

Base Information

• Chemical Name: N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine
• CAS No.: 529495-83-8
• Molecular Formula: C₂₀H₂₅N₃O₄S₃
• Molecular Weight: 467.634
• Mol file: 529495-83-8.mol

Synonyms:N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

Chemical Property of N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

There total 6 articles about N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-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: 75.0%

N-benzoyl-1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-82-7) → N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-83-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one (110171-24-9) → N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-83-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 81 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: DIBAL / toluene; hexane / 1 h / -70 °C

3.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

4.1: HMDS; (NH₄)2SO₄ / Heating

4.2: 51 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

5.1: 73 percent / HOBt / dimethylformamide / 20 °C

6.1: 75 percent / TBAF / tetrahydrofuran / 2 h

With pyridine; ammonium sulfate; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; benzotriazol-1-ol; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-ol → N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

2.1: HMDS; (NH₄)2SO₄ / Heating

2.2: 51 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

3.1: 73 percent / HOBt / dimethylformamide / 20 °C

4.1: 75 percent / TBAF / tetrahydrofuran / 2 h

With pyridine; ammonium sulfate; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00460-1

upstream raw materials:

N-benzoyl-1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Downstream raw materials:

N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)