Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)

Base Information

• Chemical Name: Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)
• CAS No.: 244642-03-3
• Molecular Formula: C17H20N5O6P
• Molecular Weight: 421.349
• Mol file: 244642-03-3.mol

Synonyms:

Chemical Property of Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate)

There total 15 articles about Thymidine, 3'-azido-3'-deoxy-, 5'-(phenylmethyl phosphonate) 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: 62.0%

3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester (124930-59-2) + benzyl alcohol (100-51-6,185532-71-2) → O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate (244642-03-3)

Guidance literature:

With pyridine; pivaloyl chloride; In acetonitrile;

DOI:10.1080/15257770008045461

Reference yield:

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) → O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate (244642-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphonic acid; pyridine; pivaloyl chloride / 0.08 h / 20 °C

2: pivaloyl chloride; pyridine / 0.17 h / 20 °C

With pyridine; phosphonic acid; pivaloyl chloride;

DOI:10.1055/s-2004-815939

Reference yield:

Phosphorous acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester dibenzyl ester → O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate (244642-03-3)

Guidance literature:

With triethylamine; In dichloromethane;

upstream raw materials:

3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester

benzyl alcohol

3'-azido-2',3'-deoxythymidine

3'-azido-2',3'-dideoxythymidine monophosphate

Downstream raw materials:

3'-azido-2',3'-deoxythymidine

3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester

O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate

Refernces

• 1、 Sun, Xiao Bin,Kang, Jian Xun,Zhao, Yu Fen. "One-pot synthesis of hydrogen phosphonate derivatives of d4T and AZT.". . p. 2414 - 2415. Retrieved 2007/10/03.