3'-Thymidylicacid, 2-chlorophenyl 2-cyanoethyl ester (9CI)

Base Information

• Chemical Name: 3'-Thymidylicacid, 2-chlorophenyl 2-cyanoethyl ester (9CI)
• CAS No.: 80817-40-9
• Molecular Formula: C19H21 Cl N3 O8 P
• Molecular Weight: 485.818
• Mol file: 80817-40-9.mol

Synonyms:

Chemical Property of 3'-Thymidylicacid, 2-chlorophenyl 2-cyanoethyl ester (9CI)

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3'-Thymidylicacid, 2-chlorophenyl 2-cyanoethyl ester (9CI)

There total 7 articles about 3'-Thymidylicacid, 2-chlorophenyl 2-cyanoethyl ester (9CI) 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:

5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) (80817-37-4) → 2'-deoxythymidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-40-9)

Guidance literature:

With zinc dibromide; In dichloromethane; isopropyl alcohol; Ambient temperature; var.: EtOAc, triazole, molecular sieves or BSA, CHCl₃, MeOH, 0 deg C, 10 min;

DOI:10.1016/S0040-4039(01)82014-1

Reference yield:

2-chlorophenyl phosphordi(1H-1-[1,2,4]triazolide) (72351-28-1) → 2'-deoxythymidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: dioxane / 2 h / 20 °C

2: 1-methylimidazole / dioxane / 3 h / 20 °C

3: benzenesulfonic acid / CHCl₃; methanol / 0.25 h / 0 °C

With benzenesulfonic acid; 1-methyl-1H-imidazole; In 1,4-dioxane; methanol; chloroform;

DOI:10.1002/hlca.19820650803

Reference yield:

[1,2,4]Triazol-1-yl-phosphonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester (76958-58-2) → 2'-deoxythymidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate (80817-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-methylimidazole / dioxane / 3 h / 20 °C

2: benzenesulfonic acid / CHCl₃; methanol / 0.25 h / 0 °C

With benzenesulfonic acid; 1-methyl-1H-imidazole; In 1,4-dioxane; methanol; chloroform;

DOI:10.1002/hlca.19820650803

upstream raw materials:

5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl β-cyanoethyl phosphate)

3-Hydroxypropionitrile

2-chlorophenyl phosphordi(1H-1-[1,2,4]triazolide)

[1,2,4]Triazol-1-yl-phosphonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester

Downstream raw materials:

Phosphoric acid (2R,3S,5R)-2-[(2-chloro-phenoxy)-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethoxy)-phosphoryloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 2-cyano-ethyl ester

5'-O-dimethoxytritylthymidylyl-(3',5')-(o-chlorophenyl)-thymidylyl-3'-β-cyanoethyl(o-chlorophenyl)phosphate

Phosphoric acid (2R,3S,5R)-2-[(2-chloro-phenoxy)-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethoxy)-phosphoryloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine

Refernces

• 1、 Ikehara,Fujimoto,Aoyama,Yanase,Matsugi,Inaoka,Tokunaga,Uesugi,Iwai,Ohtsuka. "Synthesis of a gene coding for human lysozyme.". . p. 2202 - 2208. Retrieved 2007/10/02.
• 2、 Denny, William A.,Leupin, Werner,Kearns, David R.. "Simplified Liquid-Phase Preparation of Four Decadeoxyribonucleotides and their Preliminary Spectroscopic Characterization". . p. 2372 - 2393. Retrieved 2007/10/02.