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

Base Information

Chemical Name:(1R,2S,3R,5S)-chloroacetic acid 5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentyl ester
CAS No.:902118-85-8
Molecular Formula:C₃₆H₃₈Cl₂N₄O₅Si
Molecular Weight:705.713
Hs Code.:

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

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Chemical Property of (1R,2S,3R,5S)-chloroacetic acid 5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentyl ester

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Technology Process of (1R,2S,3R,5S)-chloroacetic acid 5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentyl ester

There total 5 articles about (1R,2S,3R,5S)-chloroacetic acid 5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentyl ester 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: 51.0%

: 902118-79-0
(1S,2S,3R,5S)-5-(tert-butyldiphenylsilanyloxy)-3-(6-chloropurin-9-yl)-2-(4-methoxybenzyloxy)cyclopentanol

: 79-11-8
chloroacetic acid

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

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 80 ℃; for 18h;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

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

Guidance literature:: Multi-step reaction with 2 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

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