5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine

Base Information

• Chemical Name: 5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine
• CAS No.: 914801-95-9
• Molecular Formula: C₃₃H₄₂F₂N₆O₁₂S
• Molecular Weight: 784.792

Synonyms:5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine

Chemical Property of 5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine

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Technology Process of 5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine

There total 6 articles about 5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine 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: 87.0%

5'-amino-5'-N,N6-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine (914801-94-8) → 5'-amino-5'-N,N6-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine (914801-95-9)

Guidance literature:

With sodium hydride; Selectfluor; In tetrahydrofuran; acetonitrile; at -10 - 0 ℃;

DOI:10.1021/ol0617289

Reference yield:

N-tert-butoxycarbonyl-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethylsulfonamide (914801-93-7) → 5'-amino-5'-N,N6-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine (914801-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / bis[4-(1H,1H,2H,2H-perfluoro-7-decyl)phenyl]phenylphosphine; bis[1H,1H,2H,2H,3H,3H-perfluoro]azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C

2: 87 percent / NaH; Selectfluor / tetrahydrofuran; acetonitrile / -10 - 0 °C

With bis[4-(1H,1H,2H,2H-perfluoro-7-decyl)phenyl]phenylphospine; bis[1H,1H,2H,2H,3H,3H-perfluoro]azodicarboxylate; sodium hydride; Selectfluor; In tetrahydrofuran; acetonitrile; 1: Mitsunobu coupling;

DOI:10.1021/ol0617289

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 5'-amino-5'-N,N6-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(1,1-difluoro-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine (914801-95-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 81 percent / DMAP; TEA / CH₂Cl₂ / 12 h / 20 °C

2.1: n-BuLi; (i-Pr)2NEt / hexane; tetrahydrofuran / 1 h / 0 °C

2.2: 71 percent / hexane; tetrahydrofuran / 3 h / 0 °C

3.1: 85 percent / bis[4-(1H,1H,2H,2H-perfluoro-7-decyl)phenyl]phenylphosphine; bis[1H,1H,2H,2H,3H,3H-perfluoro]azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C

4.1: 87 percent / NaH; Selectfluor / tetrahydrofuran; acetonitrile / -10 - 0 °C

With bis[4-(1H,1H,2H,2H-perfluoro-7-decyl)phenyl]phenylphospine; dmap; n-butyllithium; bis[1H,1H,2H,2H,3H,3H-perfluoro]azodicarboxylate; TEA; sodium hydride; Selectfluor; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 3.1: Mitsunobu coupling;

DOI:10.1021/ol0617289

upstream raw materials:

5'-amino-5'-N,N⁶-di-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylidene-5'-N-[(2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethyl)sulfonyl]adenosine

N-tert-butoxycarbonyl-2-(2-(methoxymethyloxy)phenyl)-2-oxo-ethylsulfonamide

di-tert-butyl dicarbonate

methyl 2-(methoxymethyloxy)benzoate

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