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

Base Information

Chemical Name:9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl]adenine
CAS No.:259256-61-6
Molecular Formula:C₂₆H₂₉N₅O₂Si
Molecular Weight:471.634
Hs Code.:

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

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

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

There total 10 articles about 9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl]adenine 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: 66.0%

: 259256-54-7
9-[(2S,3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

: 259256-61-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl]adenine

Guidance literature:: With pyridine; dihydrogen peroxide; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1080/07328319908044642

Reference yield:

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

: 259256-61-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl]adenine

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 69 percent / NH₃ / methanol / 20 h / 80 °C

4: 66 percent / aq. H₂O₂; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; 1: Acetylation / 2: Substitution / 3: Substitution / 4: Elimination;
DOI:10.1080/07328319908044642

Reference yield:

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

: 259256-61-6
9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl]adenine

Guidance literature:: Multi-step reaction with 2 steps

1: 69 percent / NH₃ / methanol / 20 h / 80 °C

2: 66 percent / aq. H₂O₂; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; ammonia; dihydrogen peroxide; In methanol; dichloromethane; 1: Substitution / 2: Elimination;
DOI:10.1080/07328319908044642