tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

Base Information

Chemical Name:tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane
CAS No.:1374851-77-0
Molecular Formula:C₃₁H₃₇FO₃Si
Molecular Weight:504.717
Hs Code.:

Synonyms:tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

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Chemical Property of tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

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Technology Process of tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

There total 10 articles about tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane 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: 63.5%

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

: 1374851-77-0
tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

Guidance literature:: With pyridine; diethylamino-sulfur trifluoride; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
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]

: 1374851-77-0
tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 5 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

5: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; dmap; diethylamino-sulfur trifluoride; 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

: 1374851-77-0
tert-butyl((1R,2S,3S,5R)-2-fluoro-3-(4-methoxybenzyloxy)-5-vinylcyclopentyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 7 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

7.1: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; diethylamino-sulfur trifluoride; 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