(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol

Base Information

Chemical Name:(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol
CAS No.:902118-90-5
Molecular Formula:C₂₆H₂₇ClF₂N₄O₂Si
Molecular Weight:529.061
Hs Code.:

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

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

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

There total 7 articles about (1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol 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: 72.0%

: 902118-89-2
(1R,2S,4S)-9-[4-(tert-butyldiphenylsilanyloxy)-3,3-difluoro-2-(4-methoxybenzyloxy)cyclopentyl]-6-chloro-9H-purine

: 902118-90-5
(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol

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

: 902118-90-5
(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol

Guidance literature:: Multi-step reaction with 5 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: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

4.1: 76 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 24 h / Heating

5.1: 72 percent / ceric ammonium nitrate / acetonitrile; H₂O / 20 h / 20 °C

With osmium(VIII) oxide; ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; di(n-butyl)tin oxide; Dess-Martin periodane; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile; benzene;
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

: 902118-90-5
(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: dibutyltin oxide / benzene / 3 h / Heating

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

2.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

3.1: 76 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 24 h / Heating

4.1: 72 percent / ceric ammonium nitrate / acetonitrile; H₂O / 20 h / 20 °C

With ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; di(n-butyl)tin oxide; Dess-Martin periodane; In dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/j.bmc.2006.03.011