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

Base Information

Chemical Name:[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl ester
CAS No.:951377-86-9
Molecular Formula:C₃₂H₅₄O₆Si₂
Molecular Weight:590.948
Hs Code.:

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

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

There total 8 articles about [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 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: 86.0%

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

: 246872-15-1
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethanol

: 951377-86-9
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 23 ℃;
DOI:10.1021/jo071146k

Reference yield:

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 951377-86-9
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

2: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

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

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5: 86 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 3: Wittig reaction;
DOI:10.1021/jo071146k

Reference yield:

: 951377-84-7
(3aR,6aS)-6-Methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

: 951377-86-9
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 23 °C

2: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

3: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

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

5: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

6: 86 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; n-butyllithium; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; 4: Wittig reaction;
DOI:10.1021/jo071146k