(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

Chemical Name:(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:193697-16-4
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Chemical Property of (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Technology Process of (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 5 articles about (2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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:

: (E)-4-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-enoic acid ethyl ester

: 193697-16-4
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / H₂ / Pd-C / ethyl acetate / 40 h

2: 95 percent / LiAlH₄ / diethyl ether / 0.67 h / Ambient temperature

3: 97 percent / I₂, PPh₃, imidazole / benzene / 0.33 h / Ambient temperature

4: 2.83 g / t-BuOK / tetrahydrofuran / 2 h / -35 - 0 °C

5: 1.33 g / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; benzene;
DOI:10.1021/ja971259t

Reference yield:

: 193697-84-6
tert-Butyl-[(2R,4aR,6S,7R,8aS)-4a,6-dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

: 193697-16-4
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h; Ambient temperature;
DOI:10.1021/ja971259t

Reference yield:

: 193697-83-5
tert-Butyl-[(2R,4aR,6S,7R,8aS)-6-(4-iodo-3-methyl-butyl)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

: 193697-16-4
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-(3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 2.83 g / t-BuOK / tetrahydrofuran / 2 h / -35 - 0 °C

2: 1.33 g / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

With potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja971259t