N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine

Base Information

• Chemical Name: N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine
• CAS No.: 188413-86-7
• Molecular Formula: C₃₄H₂₉N₃O₉
• Molecular Weight: 623.619
• Mol file: 188413-86-7.mol

Synonyms:N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine

Chemical Property of N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine

There total 4 articles about N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine 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: 65.0%

4-N-Acetylcytosine (14631-20-0) + 5-((benzoyloxy)methyl)-3-vinyltetrahydrofuran-2,3,4-triyl tribenzoate (188413-91-4) → N4-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine (188413-86-7)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In acetonitrile; Heating;

DOI:10.1021/jo961893+

Reference yield:

benzoyl chloride (98-88-4) → N4-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine (188413-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CeCl₃, 2.) DMAP, Et₃N

2: bis(trimethylsilyl)acetamide, SnCl₄ / acetonitrile / 3 h / Heating

With dmap; cerium(III) chloride; tin(IV) chloride; bis-(trimethylsilyl)acetamide; triethylamine; In acetonitrile;

DOI:10.1080/07328319708006205

Reference yield:

1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose (157037-56-4) → N4-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine (188413-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CeCl₃, 2.) DMAP, Et₃N

2: bis(trimethylsilyl)acetamide, SnCl₄ / acetonitrile / 3 h / Heating

With dmap; cerium(III) chloride; tin(IV) chloride; bis-(trimethylsilyl)acetamide; triethylamine; In acetonitrile;

DOI:10.1080/07328319708006205

upstream raw materials:

4-N-Acetylcytosine

5-((benzoyloxy)methyl)-3-vinyltetrahydrofuran-2,3,4-triyl tribenzoate

C₃₅H₂₈O₉

benzoyl chloride

Refernces

• 1、 Harry-O'kuru,Smith,Wolfe. "A short, flexible route toward 2'-C-branched ribonucleosides". . p. 1754 - 1759. Retrieved 2007/10/03.