N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

Base Information

• Chemical Name: N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine
• CAS No.: 142102-28-1
• Molecular Formula: C₂₆H₃₅N₃O₆S₄Si
• Molecular Weight: 641.93
• Mol file: 142102-28-1.mol

Synonyms:N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

Chemical Property of N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

There total 2 articles about N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine 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:

N4-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine (72409-20-2) → N4-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine (142102-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, imidazole / 1.) THF, 45 min, 2.) THF, 30 min

2: tetrahydrofuran / 0.5 h

With 1H-imidazole; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jm00093a003

Reference yield:

Dithiocarbonic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-dithiocarboxyoxy-tetrahydro-furan-3-yl] ester + methyl iodide (74-88-4) → N4-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine (142102-28-1)

Guidance literature:

In tetrahydrofuran; for 0.5h; Yield given;

DOI:10.1021/jm00093a003

Reference yield: 65.0%

N4-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine (142102-28-1) → N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;

DOI:10.1021/jm00093a003

upstream raw materials:

methyl iodide

N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine

Downstream raw materials:

N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

N⁴-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine

N⁴-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine 5'-dimethyl phosphate

Phenyl-phosphonic acid mono-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia