3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 2-chlorophenyl 2-cyanoethyl ester

Base Information

• Chemical Name: 3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 2-chlorophenyl 2-cyanoethyl ester
• CAS No.: 80817-37-4
• Molecular Formula: C40H39ClN3O10P
• Molecular Weight: 788.191
• European Community (EC) Number: 279-565-2
• DSSTox Substance ID: DTXSID001131276
• Nikkaji Number: J320.319K
• Mol file: 80817-37-4.mol

Synonyms:EINECS 279-565-2;80817-37-4;3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 2-chlorophenyl 2-cyanoethyl ester;IJQNVUYRCQVJQH-JNTXQERPSA-;IJQNVUYRCQVJQH-JNTXQERPSA-N;DTXSID001131276;2-Chlorophenyl 2-cyanoethyl 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-thymidylate;InChI=1/C40H39ClN3O10P/c1-27-25-44(39(46)43-38(27)45)37-24-35(54-55(47,51-23-9-22-42)53-34-13-8-7-12-33(34)41)36(52-37)26-50-40(28-10-5-4-6-11-28,29-14-18-31(48-2)19-15-29)30-16-20-32(49-3)21-17-30/h4-8,10-21,25,35-37H,9,23-24,26H2,1-3H3,(H,43,45,46)/t35-

Chemical Property of 3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 2-chlorophenyl 2-cyanoethyl ester

Chemical Property:

• PSA: 170.14000
• LogP: 7.31438
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 16
• Exact Mass: 787.2061591
• Heavy Atom Count: 55
• Complexity: 1400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(=O)(OCCC#N)OC6=CC=CC=C6Cl
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(=O)(OCCC#N)OC6=CC=CC=C6Cl

Technology Process of 3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 2-chlorophenyl 2-cyanoethyl ester

There total 10 articles about 3'-Thymidylic acid, 5'-O-(bis(4-methoxyphenyl)phenylmethyl)-, 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: 83.0%

cyclohexylammonium 2-chlorophenyl 2-cyanoethyl phosphate (96404-99-8) + 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) (80817-37-4)

Guidance literature:

With 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; In pyridine; for 0.5h;

DOI:10.1055/s-1984-30834

Reference yield:

2-chlorophenyl dichlorophosphate (15074-54-1) → 5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) (80817-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dioxane / 1 h / 20 °C

2: dioxane / 2 h / 20 °C

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

With triethylamine; 1-methyl-1H-imidazole; In 1,4-dioxane;

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) + 3-Hydroxypropionitrile (109-78-4) → 5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) (80817-37-4)

Guidance literature:

With 1-methyl-1H-imidazole;

DOI:10.1248/cpb.34.2202

upstream raw materials:

cyclohexylammonium 2-chlorophenyl 2-cyanoethyl phosphate

5'-O-(4-4'-dimethoxytrityl)thymidine

bis(benzotriazol-1-yl)(2-chlorophenyl)phosphate

3-Hydroxypropionitrile

Downstream raw materials:

C₆₀H₆₀Cl₂N₈O₁₇P₂

C₅₉H₅₅Cl₂N₅O₁₇P₂*C₆H₁₅N

C₆₂H₅₈Cl₂N₆O₁₇P₂

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、 Yamada, Kohji,Dohmori, Renzo. "A Convenient Synthesis of Cyclohexylammonium 2-Chlorophenyl 2-Cyanoethyl Phosphate". . p. 333 - 335. Retrieved 2007/10/02.