(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

Base Information

Chemical Name:(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine
CAS No.:479036-14-1
Molecular Formula:C₃₂H₃₁ClF₂N₄OSSeSi
Molecular Weight:700.186
Hs Code.:

Synonyms:(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

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Chemical Property of (-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

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Technology Process of (-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

There total 12 articles about (-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine 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:

: 149712-96-9
2-fluoro-6-chloropurine

: 398133-34-1
(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

: 479036-14-1
(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -25 - 40 ℃; for 16h;
DOI:10.1021/jm020376i

Reference yield:

: 34837-55-3
Phenylselenyl bromide

: 479036-14-1
(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: TMSCl / tetrahydrofuran / 20 °C

1.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

2.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

3.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: TMSOTf / 1,2-dichloro-ethane / 16 h / -25 - 40 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; TEA; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jm020376i

Reference yield:

: 1651-29-2
6-chloro-2-fluoropurine

: 479036-14-1
(-)-9-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-6-chloro-2-fluoropurine

Guidance literature:: Multi-step reaction with 2 steps

1: ammonium sulfate / 5 h / Heating

2: TMSOTf / 1,2-dichloro-ethane / 16 h / -25 - 40 °C

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;
DOI:10.1021/jm020376i