(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Base Information

Chemical Name:(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
CAS No.:438627-73-7
Molecular Formula:C₂₂H₃₆O₆Si
Molecular Weight:424.61
Hs Code.:

Synonyms:(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Chemical Property of (3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Technology Process of (3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

There total 1 articles about (3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 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: 80.0%

: 2859-78-1
4-Bromoveratrole

: 288269-05-6
(3aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

: 438627-73-7
(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(02)00033-3

Reference yield: 94.0%

: 438627-73-7
(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

: 438627-74-8
(3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

: 438627-73-7
(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

: 438627-90-8
[(S)-3-(3,4-Dimethoxy-phenyl)-3-formyl-6-oxo-heptyl]-methyl-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

2: pyridinium chlorochromate; NaOAc

3: acetic acid / 40 °C

4: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

5: 76 percent / decahydronaphthalene / 220 °C

6: H₂ / Pd-C / ethyl acetate

7: p-TsOH / methanol / Heating

8: 88 percent / Dess-Martin periodinane / CH₂Cl₂

9: CeCl₃ / tetrahydrofuran / -20 °C

10: Me₃Al / tetrahydrofuran / Heating

11: LiAlH₄ / dioxane / Heating

12: Huenig base / CH₂Cl₂

13: NaIO₄ / tetrahydrofuran; H₂O

With sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; ethyl acetate; decalin; 5: Eschenmoser reaction;
DOI:10.1016/S0040-4039(02)00033-3