N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Base Information

• Chemical Name: N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide
• CAS No.: 211919-84-5
• Molecular Formula: C₂₃H₂₁N₅O₃S
• Molecular Weight: 447.517

Synonyms:N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Chemical Property of N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Chemical Property:

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Technology Process of N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

There total 2 articles about N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 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: 51.0%

thiophenol (108-98-5) + N-benzoyl-5-tosyl-2'-deoxyadenosine (35824-20-5) → N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide (211919-84-5)

Guidance literature:

With sodium methylate; In methanol; for 2h; Heating;

DOI:10.1021/jo980083q

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide (211919-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / pyridine / 24 h / -20 °C

2: 51 percent / CH₃ONa / methanol / 2 h / Heating

With sodium methylate; In pyridine; methanol;

DOI:10.1021/jo980083q

Reference yield: 51.0%

N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide (211919-84-5) → N6-benzoyl-5',8-cyclo-2',5'-dideoxyadenosine (211919-85-6)

Guidance literature:

With triethyl phosphite; In acetonitrile; for 10h; Irradiation;

DOI:10.1021/jo980083q

upstream raw materials:

thiophenol

N-benzoyl-5-tosyl-2'-deoxyadenosine

N₆-benzoyl-2'-deoxyadenosine

Downstream raw materials:

N⁶-benzoyl-5',8-cyclo-2',5'-dideoxyadenosine

N⁵-benzoyl-3'-O-(tert-butyldimethylsilyl)-5',8-cyclo-2',5-dideoxyadenosine

(5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine

N⁶-benzoyl-3'-O-(tert-butyldimethylsilyl)-5',8-cyclo-5'-oxo-2'-deoxyadenosine

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