1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-

Base Information

• Chemical Name: 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-
• CAS No.: 22432-95-7
• Molecular Formula: C8H12 N4 O4
• Molecular Weight: 228.208
• European Community (EC) Number: 815-973-4
• NSC Number: 127717,127716
• DSSTox Substance ID: DTXSID60859718
• Wikidata: Q27166965
• ChEMBL ID: CHEMBL117470
• Mol file: 22432-95-7.mol

Synonyms:2' Deoxy 5 azacytidine;2'-deoxy-5-azacytidine;5 Aza 2' deoxycytidine;5 Azadeoxycytidine;5 Deoxyazacytidine;5-aza-2'-deoxycytidine;5-AzadC;5-azadeoxycytidine;5-deoxyazacytidine;5AzadC;AzadC compound;Compound, AzadC;Dacogen;decitabine;decitabine mesylate;Mesylate, Decitabine;NSC 127716;NSC-127716;NSC127716

Chemical Property of 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-

Chemical Property:

• Melting Point: >174°C (dec.)
• Boiling Point: 485.8°Cat760mmHg
• PKA: 14.02±0.60(Predicted)
• Flash Point: 247.6°C
• PSA: 123.49000
• Density: 1.9g/cm³
• LogP: -1.55760
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly, Heated), Water
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 228.08585488
• Heavy Atom Count: 16
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

α-Decitabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
• Uses: α-Decitabine is shown to inhibit DNA methylation resulting in an effective anticancer agent. 2-Deoxy-D-α-ribopyranosyl-5-azacytosine is an isomer of 2-Deoxy-D-β-ribopyranosyl-5-azacytosine (D253525), an impurity of Decitabine and potentially carcinogenic.

Technology Process of 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-

There total 28 articles about 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 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-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0) → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

With ammonia; Alcoholic medium;

Reference yield: 89.3%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1-chloro-2-deoxy-D-ribofuranose (80184-05-0) → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

1-chloro-2-deoxy-D-ribofuranose; With cobalt(II) nitrate; 1,1'-bi-2-naphthol; In N,N-dimethyl-formamide; at 60 ℃; Inert atmosphere;

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; With triethylamine; In N,N-dimethyl-formamide; at 40 ℃; Temperature; Concentration; Reagent/catalyst;

Reference yield: 78.5%

1-<3,5-bis(Fmoc)-2'-deoxyribofuranosyl>-5-azacytidine → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

With pyridine; triethylamine; at 20 ℃; for 2h;

upstream raw materials:

N-(formylamidino)-N'-β-D-2-deoxyribofuranosylurea

decitabine monohydrate

5-azacytosine

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

Downstream raw materials:

2'-deoxy-β-D-5-azacytidine 5'-monophosphate

5-aza-2'-deoxycytidine

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-5-azacytidine

guadecitabine sodium salt

Refernces

• 1、 Lin,Momparler,Rivard. "High-performance liquid chromatographic analysis of chemical stability of 5-aza-2'-deoxycytidine". . p. 1228 - 1232. Retrieved 1981.
• 2、 -. "Decitabine intermediate compound V". Paragraph 0042; 0096-0103. . Retrieved 2021/01/24.
• 3、 -. "2-deoxy-D-ribose derivative". Paragraph 0086-0090. . Retrieved 2020/08/09.