2'-Deoxyzebularine

Base Information

• Chemical Name: 2'-Deoxyzebularine
• CAS No.: 22003-30-1
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.205
• Nikkaji Number: J675.891F
• Mol file: 22003-30-1.mol

Synonyms:2'-deoxyzebularine

Chemical Property of 2'-Deoxyzebularine

Chemical Property:

• Vapor Pressure: 5.37E-10mmHg at 25°C
• Refractive Index: 1.664
• Boiling Point: 450.2°Cat760mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 226.1°C
• PSA: 84.58000
• Density: 1.57g/cm³
• LogP: -1.11600
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 212.07970687
• Heavy Atom Count: 15
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

β-2’-DeoxyZebularine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC=NC2=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC=NC2=O)CO)O
• Uses: β-2’-Deoxy Zebularine is a metabolite of Zebularine (Z276000) and can be used as an inhibitor of human deoxycytidylate deaminase.

Technology Process of 2'-Deoxyzebularine

There total 4 articles about 2'-Deoxyzebularine 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: 95.0%

1-<2'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon (68753-36-6) → 1-β-D-deoxyribofuranosyl-1,2-dihydropyrimidin-2-one (6710-47-0,22003-30-1,68780-64-3,22003-08-3,83468-53-5)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2014.03.018

Reference yield:

Phosphoric acid mono-[(2R,3S,5R)-3-hydroxy-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester; compound with ammonia → 1-β-D-deoxyribofuranosyl-1,2-dihydropyrimidin-2-one (6710-47-0,22003-30-1,68780-64-3,22003-08-3,83468-53-5)

Guidance literature:

With poison of Crotalus adamanteus; alkaline phosphatase;

DOI:10.1002/hlca.19800630842

Reference yield:

1-(2'-desoxy-β-D-ribofuranosyl)-2(1H)-pyrimidinon-5'-O-triphosphat (Natriumsalz) → 1-β-D-deoxyribofuranosyl-1,2-dihydropyrimidin-2-one (6710-47-0,22003-30-1,68780-64-3,22003-08-3,83468-53-5)

Guidance literature:

With alkaline phosphatase;

DOI:10.1002/hlca.19800630842

upstream raw materials:

1-<2'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon

Downstream raw materials:

2'-deoxyzebularine 5'-[phenyl(benzoxy-L-alaninyl)]phosphate

2'-deoxyzebularine 5'-[phenyl(methoxy-L-alaninyl)]phosphate

2'-deoxyzebularine 5'-[4-chlorophenyl(ethoxy-L-alaninyl)]phosphate

2'-deoxyzebularine 3',5'-bis[4-chlorophenyl(ethoxy-L-alaninyl)]phosphate

Refernces

• 1、 Altermatt, Rolf,Tamm, Christoph. "53. Nucleoside und Nucleotide. Teil 22. Synthese eines Tridecanucleosiddodecaphosphats, das die unnatuerliche Base 2(1H)-Pyrimidinon enthaelt". . p. 475 - 483. Retrieved 2007/10/02.