3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine

Base Information

• Chemical Name: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine
• CAS No.: 1034301-08-0
• Molecular Formula: C22H18Cl2N4O6
• Molecular Weight: 505.314
• Mol file: 1034301-08-0.mol

Synonyms:4-Amino-1-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-beta-D-ribofuranosyl]-1

Chemical Property of 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine

Chemical Property:

• Boiling Point: 642.6 °C at 760 mmHg
• PKA: 3.38±0.20(Predicted)
• Flash Point: 342.4 °C
• PSA: 136.62000
• Density: 1.58 g/cm³
• LogP: 3.23980
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Very Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-1-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl]-1,3,5-triazin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Amino-1-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl]-1,3,5-triazin-2(1H)-one (Decitabine USP Related Compound B) is a derivative of β-Decitabine (A796950) which is used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.

Technology Process of 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine

There total 7 articles about 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine 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: 95.1%

C9H22N4OSi2 + 1-chloro-3,5-di-O-p-chlorobenzoyl-2-deoxy-D-ribofuranose → 1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0)

Guidance literature:

In dichloromethane; at 0 ℃; for 3h; Temperature;

Reference yield: 35.0%

C9H22N4OSi2 + methyl 3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranoside → 1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 - 85 ℃; for 5h;

Reference yield:

5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate (3601-90-9) + C6H12N4OSi → 1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃;

upstream raw materials:

3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine

5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate

2-Deoxy-D-ribose

Downstream raw materials:

5-aza-2'-deoxycytidine

Refernces

• 1、 -. "Synthetic method of decitabine". Paragraph 0050; 0051; 0056; 0057. . Retrieved 2019/08/01.
• 2、 -. "SYNTHESIS OF NUCLEOSIDES". Paragraph 0054. . Retrieved 2014/05/20.