N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine

Base Information

• Chemical Name: N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine
• CAS No.: 753456-21-2
• Molecular Formula: C₂₉H₃₆N₄O₉S
• Molecular Weight: 616.692

Synonyms:N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine

Chemical Property of N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine

Chemical Property:

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Technology Process of N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine

There total 5 articles about N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine 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: 71.0%

2,2,5,5-tetramethyl-3-oxopyrrolidine (5167-85-1) + N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine (91592-66-4) → N4-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine (753456-21-2)

Guidance literature:

2,2,5,5-tetramethyl-3-oxopyrrolidine; With thionyl chloride; triethylamine; In acetonitrile; at 5 ℃; for 0.166667h;

N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine; In dichloromethane; acetonitrile; at 25 ℃; for 5h;

DOI:10.1021/ja048377i

Reference yield:

2,2,5,5-tetramethyl-3-pyrroline-3-carboxamide (19805-75-5) → N4-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine (753456-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 40 percent / Br; aq. NaOH / 1 h / 100 °C

2.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C

2.2: 71 percent / acetonitrile; CH₂Cl₂ / 5 h / 25 °C

With sodium hydroxide; thionyl chloride; bromine; triethylamine; In acetonitrile; 1.1: Hofmann rearrangement;

DOI:10.1021/ja048377i

Reference yield:

(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl-4-oxopentanoate (93134-38-4) → N4-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-levulinyl-2'-deoxycytidine (753456-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 2 h / 25 °C

2.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C

2.2: 71 percent / acetonitrile; CH₂Cl₂ / 5 h / 25 °C

With thionyl chloride; acetic acid; triethylamine; In acetonitrile;

DOI:10.1021/ja048377i

upstream raw materials:

2,2,5,5-tetramethyl-3-oxopyrrolidine

N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine

2,2,5,5-tetramethyl-3-pyrroline-3-carboxamide

(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl-4-oxopentanoate

Downstream raw materials:

N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-2'-deoxycytidine

N⁴-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxycytidine

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