(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

Base Information

Chemical Name:(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol
CAS No.:1374851-75-8
Molecular Formula:C₃₁H₃₈O₄Si
Molecular Weight:502.726
Hs Code.:

Synonyms:(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

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Chemical Property of (1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

Chemical Property:

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Technology Process of (1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

There total 9 articles about (1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol 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:

: 1374851-76-9
(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentyl 2-chloroacetate

: 1374851-75-8
(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

Guidance literature:: With lithium hydroxide; In methanol; at 25 ℃; for 2h;
DOI:10.1016/j.tet.2012.03.023

Reference yield:

: 1009810-93-8
(3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane]

: 1374851-75-8
(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogenchloride / methanol / 25 °C

2: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C

4: lithium hydroxide / methanol / 2 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 3: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023

Reference yield:

: 1374851-71-4
(3aR,6R,6aR)-6-vinyldihydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one

: 1374851-75-8
(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate / 1 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 3 h / 0 - 20 °C

3.1: hydrogenchloride / methanol / 25 °C

4.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C

6.1: lithium hydroxide / methanol / 2 h / 25 °C

With 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 5.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023