3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine

Base Information

• Chemical Name: 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine
• CAS No.: 343263-79-6
• Molecular Formula: C₄₂H₄₂N₂O₈Se
• Molecular Weight: 781.764

Synonyms:3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine

Chemical Property of 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine

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Technology Process of 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine

There total 8 articles about 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine 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: 78.0%

2,2-dimethylpropanoic anhydride (1538-75-6) + C37H34N2O7Se → 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine (343263-79-6)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(01)00203-4

Reference yield:

diphenyl diselenide (1666-13-3) → 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine (343263-79-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.25 h / 20 °C

1.2: 94 percent / tetrahydrofuran / 0.25 h / -20 °C

2.1: 93 percent / dimethylformamide; H₂O / 3 h / 100 °C

3.1: 97 percent / NH₃ / tetrahydrofuran; methanol / 42 h / 20 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -80 °C

5.1: LHMDS; 18-crown-6 / tetrahydrofuran / 1.25 h / 20 °C

6.1: 91 percent / m-CPBA / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 78 percent / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; ammonia; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.1: Horner-Emmons reaction / 7.1: Pummerer reaction;

DOI:10.1016/S0040-4020(01)00203-4

Reference yield:

2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (101527-55-3) → 3'-C-(E)-(carbomethoxy)methylene-3'-deoxy-2'-O-pivaloyl-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine (343263-79-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.25 h / 20 °C

1.2: 94 percent / tetrahydrofuran / 0.25 h / -20 °C

2.1: 93 percent / dimethylformamide; H₂O / 3 h / 100 °C

3.1: 97 percent / NH₃ / tetrahydrofuran; methanol / 42 h / 20 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -80 °C

5.1: LHMDS; 18-crown-6 / tetrahydrofuran / 1.25 h / 20 °C

6.1: 91 percent / m-CPBA / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 78 percent / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; ammonia; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.1: Horner-Emmons reaction / 7.1: Pummerer reaction;

DOI:10.1016/S0040-4020(01)00203-4

upstream raw materials:

2,2-dimethylpropanoic anhydride

diphenyl diselenide

2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

2'-deoxy-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine

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