(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

Base Information

Chemical Name:(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol
CAS No.:902118-86-9
Molecular Formula:C₃₄H₃₉N₅O₄Si
Molecular Weight:609.8
Hs Code.:

Synonyms:(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

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Chemical Property of (1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

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Technology Process of (1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

There total 6 articles about (1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol 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: 74.0%

: 902118-85-8
(1R,2S,3R,5S)-chloroacetic acid 5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentyl ester

: 902118-86-9
(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

Guidance literature:: With ammonia; In methanol; at 75 ℃; for 24h;
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

: 902118-86-9
(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

Guidance literature:: Multi-step reaction with 4 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

With osmium(VIII) oxide; di-isopropyl azodicarboxylate; ammonia; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; water; acetone; 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

: 902118-86-9
(1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)cyclopentanol

Guidance literature:: Multi-step reaction with 3 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

With di-isopropyl azodicarboxylate; ammonia; di(n-butyl)tin oxide; triphenylphosphine; In tetrahydrofuran; methanol; benzene; 2.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2006.03.011