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

Base Information

Chemical Name:9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine
CAS No.:259256-53-6
Molecular Formula:C₃₂H₃₃ClN₄O₂SeSi
Molecular Weight:648.138
Hs Code.:

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

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

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

There total 8 articles about 9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine 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: 88.0%

: 32865-86-4
6-chloro-9-trimethylsilylpurine

: 189818-64-2
1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

: 259256-53-6
9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -22 ℃;
DOI:10.1080/07328319908044642

Reference yield:

: (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol

: 259256-53-6
9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 88 percent / TMSOTf / 1,2-dichloro-ethane / -22 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; 1,2-dichloro-ethane; 1: Acetylation / 2: Substitution;
DOI:10.1080/07328319908044642

Reference yield:

: 190078-48-9
(3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-dihydro-furan-2-one

: 259256-53-6
9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine

Guidance literature:: Multi-step reaction with 4 steps

1: DBU

2: DIBAL-H / toluene / 1.5 h / -78 °C

3: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

4: 88 percent / TMSOTf / 1,2-dichloro-ethane / -22 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; 1,2-dichloro-ethane; toluene; 1: Isomerization / 2: Reduction / 3: Acetylation / 4: Substitution;
DOI:10.1080/07328319908044642