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

Base Information

Chemical Name:(1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentyl 2-chloroacetate
CAS No.:1374851-76-9
Molecular Formula:C₃₃H₃₉ClO₅Si
Molecular Weight:579.208
Hs Code.:

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

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

Chemical Property:

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

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

: 1374851-74-7
(1S,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentanol

: 79-11-8
chloroacetic acid

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

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -40 - 60 ℃; for 24h;
DOI:10.1016/j.tet.2012.03.023

Reference yield:

: 1009810-90-5
2,3-(cyclopentylidenedioxy)-4-vinylcyclopentanol

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

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 3 h / 0 - 20 °C

2.1: hydrogenchloride / methanol / 25 °C

3.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

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

With 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023

Reference yield:

: 1009810-89-2
(3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.5 h / -78 °C

1.2: 5 h / -78 °C

2.1: tetrabutyl ammonium fluoride; ammonium chloride / tetrahydrofuran; water / 0.5 h / 20 °C

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

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

4.2: 3 h / 0 - 20 °C

5.1: hydrogenchloride / methanol / 25 °C

6.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

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

With 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium hydride; ammonium chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 7.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023