(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

Base Information

Chemical Name:(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol
CAS No.:902118-88-1
Molecular Formula:C₂₆H₃₀FN₅O₂Si
Molecular Weight:491.64
Hs Code.:

Synonyms:(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

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Chemical Property of (1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

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Technology Process of (1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

There total 8 articles about (1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol 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: 71.0%

: 902118-87-0
(1R,2S,3S,4S)-9-[4-(tert-butyldiphenylsilanyloxy)-3-fluoro-2-(4-methoxybenzyloxy)cyclopentyl]-9H-purin-6-ylamine

: 902118-88-1
(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 20h;
DOI:10.1016/j.bmc.2006.03.011

Reference yield:

: 902118-76-7
9-[(1R,4S)-4-(tert-butyldiphenylsilanyloxy)cyclopent-2-enyl]-6-chloro-9H-purine

: 902118-88-1
(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O; acetone / 24 h / 20 °C

2.1: dibutyltin oxide / benzene / 3 h / Heating

2.2: 74 percent / tetrabutylammonium bromide / benzene / 3 h / Heating

3.1: 51 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 80 °C

4.1: 74 percent / NH₃ / methanol / 24 h / 75 °C

5.1: 67 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / -78 - 20 °C

6.1: 71 percent / ceric ammonium nitrate / acetonitrile; H₂O / 20 h / 20 °C

With osmium(VIII) oxide; ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; ammonia; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; benzene; 3.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2006.03.011

Reference yield:

: 902118-77-8
(1S,2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)cyclopentane-1,2-diol

: 902118-88-1
(1S,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2-fluorocyclopentanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: dibutyltin oxide / benzene / 3 h / Heating

1.2: 74 percent / tetrabutylammonium bromide / benzene / 3 h / Heating

2.1: 51 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 80 °C

3.1: 74 percent / NH₃ / methanol / 24 h / 75 °C

4.1: 67 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / -78 - 20 °C

5.1: 71 percent / ceric ammonium nitrate / acetonitrile; H₂O / 20 h / 20 °C

With ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; ammonia; di(n-butyl)tin oxide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene; 2.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2006.03.011