N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine

Base Information

• Chemical Name: N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine
• CAS No.: 298699-72-6
• Molecular Formula: C₃₁H₃₆N₄O₁₀
• Molecular Weight: 624.648

Synonyms:N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine

Chemical Property of N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine

Chemical Property:

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Technology Process of N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine

There total 2 articles about N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}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: 73.0%

N4-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (149989-44-6) + 3-{[2-(2-nitrophenyl)propoxy]carbonyl}-1-methyl-1H-imidazolium chloride → N4-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine (298699-72-6)

Guidance literature:

With 4 A molecular sieve; In dichloromethane; at 0 ℃;

DOI:10.1002/1522-2675(20010711)84:7<2089::AID-HLCA2089>3.0.CO;2-0

Reference yield:

2-(2-nitrophenyl)propyl carbonochloridate (154187-40-3) → N4-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine (298699-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem mol. sieves / CH₂Cl₂ / 0.5 h / 0 °C

2: 73 percent / 4 Angstroem mol. sieves / CH₂Cl₂ / 0 °C

With 4 A molecular sieve; In dichloromethane;

DOI:10.1002/1522-2675(20010711)84:7<2089::AID-HLCA2089>3.0.CO;2-0

Reference yield: 81.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + N4-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine (298699-72-6) → N4-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine 5'-(2-cyanoethyl diisopropylphosphoramidite)

Guidance literature:

With pyridine hydrochloride; In acetonitrile; for 1h;

DOI:10.1002/1522-2675(20010711)84:7<2089::AID-HLCA2089>3.0.CO;2-0

upstream raw materials:

N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

2-(2-nitrophenyl)propyl carbonochloridate

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