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

Base Information

• Chemical Name: (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol
• CAS No.: 438627-74-8
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347

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

Chemical Property of (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol

Chemical Property:

Purity/Quality:

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Technology Process of (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol

There total 3 articles about (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol 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: 94.0%

(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(3,4-dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (438627-73-7) → (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol (438627-74-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

4-Bromoveratrole (2859-78-1) → (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol (438627-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

(3aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one (288269-05-6) → (3aS,4S,6R,6aS)-4-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-diol (438627-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00033-3

upstream raw materials:

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

4-Bromoveratrole

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

Downstream raw materials:

(3aR,6S,6aS)-6-(3,4-Dimethoxy-phenyl)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

(3aR,6aR)-6-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

(3aS,4S,6aR)-6-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

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