N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine

Base Information

• Chemical Name: N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine
• CAS No.: 1384260-61-0
• Molecular Formula: C₃₀H₃₀Cl₄N₄O₇Si
• Molecular Weight: 728.488
• Mol file: 1384260-61-0.mol

Synonyms:N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine

Chemical Property of N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine

There total 4 articles about N₄-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine 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: 47.0%

N4-benzoyl-5'-tetrachlorophthalimido-5'-deoxycytidine (1384260-60-9) + tert-butyldimethylsilyl chloride (18162-48-6) → N4-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine (1384260-61-0)

Guidance literature:

N₄-benzoyl-5'-tetrachlorophthalimido-5'-deoxycytidine; With pyridine; silver nitrate; In N,N-dimethyl-formamide; for 0.166667h;

tert-butyldimethylsilyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2012.05.055

Reference yield:

N4-benzoyl-5'-tetrachlorophthalimido-2',3'-O-isopropylidene-5'-deoxycytidine (1384260-59-6) → N4-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine (1384260-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / water / 2 h / 20 °C

2.1: pyridine; silver nitrate / N,N-dimethyl-formamide / 0.17 h

2.2: 24 h / 20 °C

With pyridine; silver nitrate; trifluoroacetic acid; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2012.05.055

Reference yield:

benzoyl chloride (98-88-4) → N4-benzoyl-2'-O-(tertbutyldimethylsilyl)-5'-tetrachlorophthalimido-5'-deoxycytidine (1384260-61-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine; chloro-trimethyl-silane

2.1: toluene-4-sulfonic acid / water; acetone / 24 h / Reflux

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 15 h / Reflux

4.1: trifluoroacetic acid / water / 2 h / 20 °C

5.1: pyridine; silver nitrate / N,N-dimethyl-formamide / 0.17 h

5.2: 24 h / 20 °C

With pyridine; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; silver nitrate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; 3.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2012.05.055

upstream raw materials:

N₄-benzoyl-5'-tetrachlorophthalimido-2',3'-O-isopropylidene-5'-deoxycytidine

N₄-benzoyl-5'-tetrachlorophthalimido-5'-deoxycytidine

tert-butyldimethylsilyl chloride

benzoyl chloride

Downstream raw materials:

N₄-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-(4-monomethoxytritylamino)-5'-deoxycytidine

N₄-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-amino-5'-deoxycytidine