5'-Thymidylic acid, 3'-azido-3'-deoxy-, monophenyl ester

Base Information

• Chemical Name: 5'-Thymidylic acid, 3'-azido-3'-deoxy-, monophenyl ester
• CAS No.: 219909-16-7
• Molecular Formula: C16H18N5O7P
• Molecular Weight: 423.322
• Mol file: 219909-16-7.mol

Synonyms:

Chemical Property of 5'-Thymidylic acid, 3'-azido-3'-deoxy-, monophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-Thymidylic acid, 3'-azido-3'-deoxy-, monophenyl ester

There total 6 articles about 5'-Thymidylic acid, 3'-azido-3'-deoxy-, monophenyl ester 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: 83.0%

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 4-nitro-benzyl ester phenyl ester (879688-49-0) → Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester phenyl ester (219909-16-7)

Guidance literature:

With triethylamine; In water; acetonitrile;

DOI:10.1016/j.bmc.2005.10.048

Reference yield:

3'-azido-3'-deoxythymidin-5'-yl phenyl hydroxy(4-nitrophenyl)methanephosphonate (879688-34-3) → Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester phenyl ester (219909-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / triethylamine / acetonitrile; H₂O

2: 83 percent / triethylamine / acetonitrile; H₂O

With triethylamine; In water; acetonitrile;

DOI:10.1016/j.bmc.2005.10.048

Reference yield:

3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester (124930-59-2) → Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester phenyl ester (219909-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; diphenyl chlorophosphate / CH₂Cl₂ / 0.33 h

2: 0.92 g / pyridine; 2,6-lutidine / CH₂Cl₂ / 0.75 h

3: 83 percent / triethylamine / acetonitrile; H₂O

4: 83 percent / triethylamine / acetonitrile; H₂O

With pyridine; 2,6-dimethylpyridine; triethylamine; chlorophosphoric acid diphenyl ester; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.bmc.2005.10.048

upstream raw materials:

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 4-nitro-benzyl ester phenyl ester

3'-azido-3'-deoxythymidin-5'-yl phenyl hydroxy(4-nitrophenyl)methanephosphonate

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

C₁₆H₁₈N₅O₆P

Downstream raw materials:

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 4-nitro-benzyl ester phenyl ester

Refernces

• 1、 Szymanska, Agnieszka,Szymczak, Marzena,Boryski, Jerzy,Stawinski, Jacek,Kraszewski, Adam,Collu, Gabriella,Sanna, Giseppina,Giliberti, Gabriele,Loddo, Roberta,Colla, Paolo La. "Aryl nucleoside H-phosphonates. Part 15: Synthesis, properties and, anti-HIV activity of aryl nucleoside 5′-α-hydroxyphosphonates". . p. 1924 - 1934. Retrieved 2007/10/03.