9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

Base Information

• Chemical Name: 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine
• CAS No.: 259261-20-6
• Molecular Formula: C₂₆H₂₈FN₅O₂Si
• Molecular Weight: 489.625
• Mol file: 259261-20-6.mol

Synonyms:9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

Chemical Property of 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

There total 9 articles about 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine 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: 88.7%

9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-2-fluoroadenine (259256-59-2) → 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine (259261-20-6)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; at 20 ℃;

DOI:10.1080/07328319908044642

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine (259261-20-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 87 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2.1: LiHMDS; Me₃SiCl / tetrahydrofuran / 0.5 h / -78 °C

2.2: 62.6 percent / tetrahydrofuran / -78 °C

3.1: DIBAL-H / toluene / 1.5 h / -78 °C

4.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

5.1: 78.3 percent / TMSOTf / 1,2-dichloro-ethane / -22 °C

6.1: 35.14 percent / NH₃ gas / 1,2-dimethoxy-ethane / 18 h

7.1: 88.7 percent / aq. H₂O₂; pyridine / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; dmap; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: Substitution / 2.1: silylation / 2.2: Substitution / 3.1: Reduction / 4.1: Acetylation / 5.1: Substitution / 6.1: Substitution / 7.1: Elimination;

DOI:10.1080/07328319908044642

Reference yield:

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5) → 9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine (259261-20-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiHMDS; Me₃SiCl / tetrahydrofuran / 0.5 h / -78 °C

1.2: 62.6 percent / tetrahydrofuran / -78 °C

2.1: DIBAL-H / toluene / 1.5 h / -78 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

4.1: 78.3 percent / TMSOTf / 1,2-dichloro-ethane / -22 °C

5.1: 35.14 percent / NH₃ gas / 1,2-dimethoxy-ethane / 18 h

6.1: 88.7 percent / aq. H₂O₂; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: silylation / 1.2: Substitution / 2.1: Reduction / 3.1: Acetylation / 4.1: Substitution / 5.1: Substitution / 6.1: Elimination;

DOI:10.1080/07328319908044642

upstream raw materials:

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

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one

tert-butylchlorodiphenylsilane