9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

Base Information

Chemical Name:9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine
CAS No.:137058-81-2
Molecular Formula:C₂₄H₃₃N₅O₅SSi
Molecular Weight:531.708
Hs Code.:

Synonyms:9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

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Chemical Property of 9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

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Technology Process of 9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

There total 5 articles about 9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)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: 84.0%

: 137058-80-1
9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-β-D-erythro-pentofuranosyl)adenine

: 98-59-9
p-toluenesulfonyl chloride

: 137058-81-2
9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 2.5h; Ambient temperature;
DOI:10.1021/jo00025a029

Reference yield:

: 65109-11-7
2',5'-bis-O-(tert-butyldimethylsilyl)adenosine

: 137058-81-2
9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂ / 1.5 h

2: 1) sodium 2-methyl-2-butoxide / 1) Et₂O, benzene, 2h, 2a) -70 to -10 deg C, 1h, 2b) 4 deg C, 48h

3: 95 percent / TFA, H₂O / 0.5 h / 0 °C

4: 84 percent / NEt₃, DMAP / CH₂Cl₂ / 2.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; water; acetic anhydride; sodium tert-pentoxide; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo00025a029

Reference yield:

: 86734-95-4
9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

: 137058-81-2
9-(2-O-(tert-butyldimethylsilyl)-3-deoxy-3-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

Guidance literature:: Multi-step reaction with 3 steps

1: 1) sodium 2-methyl-2-butoxide / 1) Et₂O, benzene, 2h, 2a) -70 to -10 deg C, 1h, 2b) 4 deg C, 48h

2: 95 percent / TFA, H₂O / 0.5 h / 0 °C

3: 84 percent / NEt₃, DMAP / CH₂Cl₂ / 2.5 h / Ambient temperature

With dmap; water; sodium tert-pentoxide; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo00025a029