(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

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Chemical Name:(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde
CAS No.:374638-42-3
Molecular Formula:C₁₈H₂₄O₆
Molecular Weight:336.385
Hs Code.:

Synonyms:(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

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Chemical Property of (S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

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Technology Process of (S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

There total 5 articles about (S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde 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: 99.0%

: 374638-41-2
(2R,4aR,6S,7R,8aS)-6-((S)-1-Hydroxy-but-3-enyl)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 374638-42-3
(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

Guidance literature:: (2R,4aR,6S,7R,8aS)-6-((S)-1-Hydroxy-but-3-enyl)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol; With ozone; In methanol; dichloromethane; at -78 ℃;

With triphenylphosphine; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(01)01204-7

Reference yield:

: 131311-02-9
(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 374638-42-3
(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 0.5 h / 20 °C

3.1: diethyl ether; pentane / 5 h / -78 °C

3.2: 92 percent / aq. H₂O₂; aq. NaOH / diethyl ether; pentane; methanol / 1 h / 20 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

5.1: O₃ / CH₂Cl₂; methanol / -78 °C

5.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 1 h / 25 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 3.1: Brown's asymmetric allylboration;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 131311-03-0
tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

: 374638-42-3
(S)-3-Hydroxy-3-((2R,4aR,6R,7R,8aS)-7-hydroxy-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 0.5 h / 20 °C

2.1: diethyl ether; pentane / 5 h / -78 °C

2.2: 92 percent / aq. H₂O₂; aq. NaOH / diethyl ether; pentane; methanol / 1 h / 20 °C

3.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 99 percent / PPh₃ / CH₂Cl₂; methanol / 1 h / 25 °C

With tetrabutyl ammonium fluoride; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 2.1: Brown's asymmetric allylboration;
DOI:10.1016/S0040-4020(02)00039-X