N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine

Base Information

• Chemical Name: N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine
• CAS No.: 123413-57-0
• Molecular Formula: C16H15 N3 O4
• Molecular Weight: 313.313
• Mol file: 123413-57-0.mol

Synonyms:N4-Benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine

Chemical Property of N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 93.45000
• Density: 1.4g/cm³
• LogP: 1.01450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine

There total 5 articles about N(4)-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine 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: 88.0%

N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4) → N4-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine (123413-57-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jm00093a003

Reference yield: 64.0%

benzoic acid anhydride (93-97-0) + 2',3'-dideoxy-2'-cytidinene (7481-88-1) → N4-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine (123413-57-0)

Guidance literature:

In 1,4-dioxane; water;

DOI:10.1248/cpb.37.2547

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 → N4-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine (123413-57-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 0.5 h

2: 65 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating

3: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1021/jm00093a003

upstream raw materials:

benzoic acid anhydride

2',3'-dideoxy-2'-cytidinene

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

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

Downstream raw materials:

Phosphoric acid (2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester phenyl ester; compound with ammonia

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

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

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

Refernces

• 1、 Mullah,Rao,Balzarini,De Clercq,Bentrude. "Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities". . p. 2728 - 2735. Retrieved 2007/10/02.