3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl ester

Base Information

• Chemical Name: 3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl ester
• CAS No.: 80817-40-9
• Molecular Formula: C19H21 Cl N3 O8 P
• Molecular Weight: 485.818
• European Community (EC) Number: 279-568-9
• DSSTox Substance ID: DTXSID701215188
• Nikkaji Number: J320.322K
• Mol file: 80817-40-9.mol

Synonyms:3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl ester;EINECS 279-568-9;80817-40-9;FHCIBQVTFJCGFG-ZKHLZZRJSA-N;DTXSID701215188

Chemical Property of 3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl ester

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 485.0754793
• Heavy Atom Count: 32
• Complexity: 846

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)OP(=O)(OCCC#N)OC3=CC=CC=C3Cl
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)OP(=O)(OCCC#N)OC3=CC=CC=C3Cl

Technology Process of 3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl ester

There total 7 articles about 3'-Thymidylic acid, 2-chlorophenyl 2-cyanoethyl 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:

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:

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

C₇₂H₇₁Cl₃N₇O₂₄P₃

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

C₆₃H₅₈Cl₂N₈O₁₆P₂