Cytidine, 2'-deoxy-N,N,5-trimethyl-

Base Information

• Chemical Name: Cytidine, 2'-deoxy-N,N,5-trimethyl-
• CAS No.: 25406-45-5
• Molecular Formula: C₁₂H₁₉N₃O₄
• Molecular Weight: 269.301
• DSSTox Substance ID: DTXSID00948256
• Nikkaji Number: J3.623.029K
• Wikidata: Q82926035
• Mol file: 25406-45-5.mol

Synonyms:4-dimethylaminothymidine;4-DMA-TH

Chemical Property of Cytidine, 2'-deoxy-N,N,5-trimethyl-

Chemical Property:

• Boiling Point: 457.3 °C at 760 mmHg
• Flash Point: 230.4 °C
• PSA: 87.82000
• Density: 1.41 g/cm³
• LogP: -0.74160
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 269.13755610
• Heavy Atom Count: 19
• Complexity: 433

Purity/Quality:

97% ^*data from raw suppliers

2''-Deoxy-N,N,5-trimethylcytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)N=C1N(C)C)C2CC(C(O2)CO)O
• Isomeric SMILES: CC1=CN(C(=O)N=C1N(C)C)[C@H]2C[C@@H]([C@H](O2)CO)O
• Uses: 2''-Deoxy-N,N,5-trimethylcytidine is used in the synthetic preparation of antiviral pyrimidine nucleosides via amide group activation, some of which are active against HIV-1 and HIV-2.

Technology Process of Cytidine, 2'-deoxy-N,N,5-trimethyl-

There total 4 articles about Cytidine, 2'-deoxy-N,N,5-trimethyl- 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: 96.0%

3’,5’-di-O-(t-butyldimethylsilyl)-N,N,5-trimethyl-2’-deoxycytidine (1107614-92-5) → N,N,5-trimethyl-2’-deoxycytidine (25406-45-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1039/C6OB02334G

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → N,N,5-trimethyl-2’-deoxycytidine (25406-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 20 °C / Sealed tube

2: tetrahydrofuran / 2 h / 20 °C / Sealed tube

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

With tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1039/C6OB02334G

Reference yield:

O4-(1H-benzotriazol-1-yl)-3’,5’-di-O-(t-butyldimethylsilyl)thymidine → N,N,5-trimethyl-2’-deoxycytidine (25406-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / 20 °C / Sealed tube

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1039/C6OB02334G

upstream raw materials:

3’,5’-di-O-(t-butyldimethylsilyl)-N,N,5-trimethyl-2’-deoxycytidine

3',5'-O-di(tert-butyldimethylsilyl)thymidine

Refernces

• 1、 Akula, Hari K.,Kokatla, Hariprasad,Andrei, Graciela,Snoeck, Robert,Schols, Dominique,Balzarini, Jan,Yang, Lijia,Lakshman, Mahesh K.. "Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products". supporting information. p. 1130 - 1139. Retrieved 2017/02/10.