3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine

Base Information

• Chemical Name: 3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine
• CAS No.: 1093283-41-0
• Molecular Formula: C₂₃H₁₉BrN₆O₅
• Molecular Weight: 539.345
• Mol file: 1093283-41-0.mol

Synonyms:3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine

Chemical Property of 3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine

There total 5 articles about 3'-azido-N₄-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine 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: 67.0%

C23H18BrN3O5 (1093283-40-9) → 3'-azido-N4-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine (1093283-41-0)

Guidance literature:

C₂₃H₁₈BrN₃O₅; With sodium azide; In N,N-dimethyl-formamide; at 130 ℃; for 2h;

With water; ammonium chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo8018889

Reference yield:

4-Bromobenzoic acid (586-76-5) → 3'-azido-N4-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine (1093283-41-0)

Guidance literature:

Multi-step reaction with 3 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / N,N-dimethyl-formamide

2: di-isopropyl azodicarboxylate; triphenylphosphine / N,N-dimethyl-formamide

3: sodium azide / N,N-dimethyl-formamide

With sodium azide; di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; 1: |Mitsunobu Displacement / 2: |Mitsunobu Displacement;

DOI:10.1002/cbic.202000450

Reference yield:

C23H20BrN3O6 → 3'-azido-N4-benzoyl-5'-O-(p-bromobenzoyl)-2',3'-dideoxycytidine (1093283-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / N,N-dimethyl-formamide

2: sodium azide / N,N-dimethyl-formamide

With sodium azide; di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; 1: |Mitsunobu Displacement;

DOI:10.1002/cbic.202000450

upstream raw materials:

C₂₃H₁₈BrN₃O₅

4-Bromobenzoic acid

2'-Deoxycytidine

N₄-benzoyl-2'-deoxycytidine

Downstream raw materials:

3’-azido N4-benzoyl 2’-deoxycytidine

Refernces

• 1、 Eisenhuth, Ralf,Richert, Clemens. "Convenient syntheses of 3′-amino-2′,3′- dideoxynucleosides, their 5′-monophosphates, and 3′-aminoterminal oligodeoxynucleotide primers". experimental part. p. 26 - 37. Retrieved 2009/04/07.