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
Hs Code.:

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

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

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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%

: 259256-59-2
9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-2-fluoroadenine

: 259261-20-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

Guidance literature:: With pyridine; dihydrogen peroxide; In dichloromethane; at 20 ℃;
DOI:10.1080/07328319908044642

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 259261-20-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

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:

: 128075-94-5
(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one

: 259261-20-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-deoxy-β-L-glycero-pent-2-enofuranosyl]-2-fluoroadenine

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