Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate

Base Information

• Chemical Name: Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate
• CAS No.: 198637-58-0
• Molecular Formula: C₄₄H₄₆N₅O₁₂PS
• Molecular Weight: 899.915
• DSSTox Substance ID: DTXSID601108839
• Mol file: 198637-58-0.mol

Synonyms:DTXSID601108839;198637-58-0;Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate

Chemical Property of Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 18
• Exact Mass: 899.26013009
• Heavy Atom Count: 63
• Complexity: 1830

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=S)(OCCC#N)OC3CC(OC3COC(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)N7C=C(C(=O)NC7=O)C)OC(=O)C
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO[P@@](=S)(OCCC#N)O[C@@H]3C[C@@H](O[C@@H]3COC(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)N7C=C(C(=O)NC7=O)C)OC(=O)C

Technology Process of Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate

There total 5 articles about Thymidine, [P(S)]-P(O)-(2-cyanoethyl)-P-thio-5'-O-(triphenylmethyl)-beta-D-threo-thymidylyl-(3'-->5')-, 3'-acetate 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: 15.0%

C44H48N5O11P → SP-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (198637-58-0) + RP-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (198637-55-7)

Guidance literature:

With sulfur;

DOI:10.1016/S0960-894X(97)10040-3

Reference yield:

3'-O-acetylthymidine (21090-30-2) → SP-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (198637-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-tetrazole / acetonitrile / 2 h / 20 °C

2: S₈ / acetonitrile; CH₂Cl₂

With 1H-tetrazole; sulfur; In dichloromethane; acetonitrile;

DOI:10.1002/1099-0690(200104)2001:8<1491::AID-EJOC1491>3.0.CO;2-3

Reference yield:

5'-O-trityldeoxyxylothymidine 3'-O-[N,N-diisopropyl-O-(2-cyanoethyl)phosphoramidite] (198637-50-2) → SP-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (198637-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-tetrazole / acetonitrile / 2 h / 20 °C

2: S₈ / acetonitrile; CH₂Cl₂

With 1H-tetrazole; sulfur; In dichloromethane; acetonitrile;

DOI:10.1002/1099-0690(200104)2001:8<1491::AID-EJOC1491>3.0.CO;2-3

upstream raw materials:

acetic acid 2-{(2-cyano-ethoxy)-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-phosphanyloxymethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

3'-O-acetylthymidine

5'-O-trityldeoxyxylothymidine 3'-O-[N,N-diisopropyl-O-(2-cyanoethyl)phosphoramidite]

5'-O-trityldeoxyxylothymidine