2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol

Base Information

• Chemical Name: 2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol
• CAS No.: 259256-64-9
• Molecular Formula: C₂₆H₃₁N₅O₃Si
• Molecular Weight: 489.649

Synonyms:2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol

Chemical Property of 2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol

Chemical Property:

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Technology Process of 2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol

There total 18 articles about 2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol 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%

9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]guanine (259256-60-5) → 2-amino-9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-ol (259256-64-9)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In benzene; at 20 ℃;

DOI:10.1080/07328319908044642

Reference yield:

(R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan → 2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one (259256-64-9)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / -78 °C

2: DIBAL-H / tetrahydrofuran / -78 °C

3: DMAP / CH₂Cl₂ / 0 °C

4: 78 percent / TMSOTf / 1,2-dichloro-ethane / 0 °C

5: NH₃ / methanol / 80 °C

6: HSC₂H₄OH, NaOMe / methanol / Heating

7: Bu₃SnH, Et₃B / benzene / Ambient temperature

With dmap; triethyl borane; trimethylsilyl trifluoromethanesulfonate; ammonia; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; 2-hydroxyethanethiol; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.1016/0960-894X(96)00293-4

Reference yield:

2-Amino-9-[(2S,3S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one (259256-60-5) → 2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one (259256-64-9)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In benzene; Ambient temperature;

DOI:10.1016/0960-894X(96)00293-4

upstream raw materials:

2-Amino-9-[(2S,3S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-2-fluoro-9H-purine

2-amino-9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine

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