4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one

Base Information

• Chemical Name: 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one
• CAS No.: 107036-52-2
• Molecular Formula: C8H12 N4 O3
• Molecular Weight: 212.208
• Mol file: 107036-52-2.mol

Synonyms:2',3'-Dideoxy-5-azacytidine

Chemical Property of 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one

Chemical Property:

• Vapor Pressure: 3.81E-08mmHg at 25°C
• Boiling Point: 402.3°Cat760mmHg
• Flash Point: 197.1°C
• Density: 1.73g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one

There total 8 articles about 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one 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: 100.0%

1-[5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-ribofuranosyl]-5-azacytosine → 2',3'-dideoxy-β-D-5-azacytidine (107036-52-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.chembiol.2019.04.010

Reference yield: 30.0%

2',3'-dideoxy-5'-O-(4,4'-dimethoxytrityl)-5-azacytidine (107036-51-1) → 2',3'-dideoxy-β-D-5-azacytidine (107036-52-2)

Guidance literature:

With silica gel; In chloroform; benzene; for 24h; Ambient temperature;

DOI:10.1021/jm00388a020

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 2',3'-dideoxy-β-D-5-azacytidine (107036-52-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / Inert atmosphere; Cooling

2.2: 16 h / 0 - 20 °C

3.1: ethylaluminum dichloride / toluene; 1,2-dichloro-ethane / 16 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; ethylaluminum dichloride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1002/mrc.4942

upstream raw materials:

2',3'-dideoxy-5'-O-(4,4'-dimethoxytrityl)-5-azacytidine

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

L-glutamic acid

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

Refernces

• 1、 Banuelos-Sanchez, Guillermo,Sanchez, Laura,Benitez-Guijarro, Maria,Sanchez-Carnerero, Valentin,Salvador-Palomeque, Carmen,Tristan-Ramos, Pablo,Benkaddour-Boumzaouad, Meriem,Morell, Santiago,Garcia-Puche, Jose L.,Heras, Sara R.,Franco-Montalban, Francisco,Tamayo, Juan A.,Garcia-Perez, Jose L.. "Synthesis and Characterization of Specific Reverse Transcriptase Inhibitors for Mammalian LINE-1 Retrotransposons". . p. 1095 - 14,1109. Retrieved 2019/08/13.
• 2、 -. "5-substituted-2',3'-dideoxycytidine compounds with anti-HTLV-III activity". . . Retrieved 2008/06/13.