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

Base Information

• Chemical Name: 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine
• CAS No.: 529495-89-4
• Molecular Formula: C₂₉H₃₉N₃O₃S₃Si
• Molecular Weight: 601.93
• Mol file: 529495-89-4.mol

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

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

There total 4 articles about 1-[5'-O-tert-butyldiphenylsilyl-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: 51.0%

Cytosine (71-30-7) + (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate (529495-78-1) → 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-89-4) + 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-α-L-erythro-pentofuranosyl]cytosine

Guidance literature:

Cytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; for 0.75h;

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

Reference yield:

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one (110171-24-9) → 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-89-4)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; ammonium sulfate; n-butyllithium; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; 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 → 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine (529495-89-4)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

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

upstream raw materials:

Cytosine

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

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

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

Downstream raw materials:

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

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

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