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

Base Information

• Chemical Name: 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
• CAS No.: 1053651-85-6
• Molecular Formula: C₄₄H₄₆N₅O₁₂P
• Molecular Weight: 867.849

Synonyms:

Chemical Property of 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

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Technology Process of 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

There total 2 articles about 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 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:

3'-O-acetylthymidine (21090-30-2) + 5'-O-trityldeoxyxylothymidine 3'-O-[N,N-diisopropyl-O-(2-cyanoethyl)phosphoramidite] (198637-50-2) → 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 (1053651-85-6)

Guidance literature:

With 1H-tetrazole; In acetonitrile; at 20 ℃; for 2h;

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

Reference yield:

5'-O-trityldeoxyxylothymidine (55612-11-8) → 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 (1053651-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

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

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

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

Reference yield:

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 (1053651-85-6) → 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; In dichloromethane; acetonitrile;

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

upstream raw materials:

3'-O-acetylthymidine

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

5'-O-trityldeoxyxylothymidine

Downstream raw materials:

S_P-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate

R_P-5'-O-trityldeoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate

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