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

Base Information

Chemical Name:(3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane]
CAS No.:1009810-93-8
Molecular Formula:C₂₀H₂₆O₄
Molecular Weight:330.424
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane]

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Technology Process of (3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane]

There total 7 articles about (3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane] 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: 86.2%

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

: 824-94-2
p-methoxybenzyl chloride

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

Guidance literature:: 2,3-(cyclopentylidenedioxy)-4-vinylcyclopentanol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h;
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

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

Guidance literature:: Multi-step reaction with 2 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

With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium hydride; In N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2012.03.023

Reference yield:

: 1374851-70-3
(3a'S,4'S,6a'R)-4'-iodomethyl-6'-methoxytetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxole]

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

Guidance literature:: Multi-step reaction with 8 steps

1.1: acetic acid; zinc / methanol / 5 h / Reflux

2.1: tetrahydrofuran; dichloromethane / -78 - 0 °C

2.2: 0 °C

3.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: manganese(IV) oxide / dichloromethane / 20 - 60 °C

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

5.2: 5 h / -78 °C

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

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

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

8.2: 3 h / 0 - 20 °C

With Grubbs catalyst first generation; methanol; manganese(IV) oxide; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; sodium hydride; ammonium chloride; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 3.1: Grubbs metathesis;
DOI:10.1016/j.tet.2012.03.023