[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

Base Information

Chemical Name:[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester
CAS No.:869476-96-0
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

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Chemical Property of [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

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Technology Process of [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

There total 13 articles about [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl 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: 92.0%

: 869476-95-9
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid

: 501-94-0
p-hydroxyphenethyl alcohol

: 869476-96-0
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol052106a

Reference yield:

: 501-94-0
p-hydroxyphenethyl alcohol

: C₁₂H₁₈O₄

: 869476-96-0
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

: C₂₀H₂₆O₅

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

Reference yield:

: 129263-68-9,828937-29-7
((3aS,4R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 869476-96-0
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridinium chlorochromate / benzene / 10.5 h / Heating

1.2: 1.16 g / pyridinium chlorochromate / benzene / 14.5 h / Heating

2.1: 85 percent / n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 23 °C

3.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

4.1: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

5.1: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

6.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

7.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; triphenylphosphine; pyridinium chlorochromate; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; toluene; benzene; 5.1: Wittig reaction / 7.1: Mitsunobu reaction;
DOI:10.1021/jo071146k