(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

Base Information

• Chemical Name: (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
• CAS No.: 374638-41-2
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 374638-41-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 100.0%

(S)-1-[(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]-but-3-en-1-ol (374638-44-5) → (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 (374638-41-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(01)01204-7

Reference yield:

(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (131311-02-9) → (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 (374638-41-2)

Guidance literature:

Multi-step reaction with 4 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

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:

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 (131311-03-0) → (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 (374638-41-2)

Guidance literature:

Multi-step reaction with 3 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

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

upstream raw materials:

(S)-1-[(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]-but-3-en-1-ol

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

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

(2R,4aR,6R,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

Downstream raw materials:

((2R,4aR,5S,7R,8aR,9aS,10aR)-4a,10a-Dimethyl-2-phenyl-5-triisopropylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-acetic acid methyl ester

3-((2R,4aR,5S,7S,8aR,9aS,10aR)-4a,10a-Dimethyl-2-phenyl-5-triisopropylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-propan-1-ol

(2R,3S,4aR,6S,8S,8aR)-6-(3-Benzyloxy-propyl)-2-hydroxymethyl-2,8a-dimethyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

[(2R,4aR,5S,7S,8aR,9aS,10aR)-7-(3-Benzyloxy-propyl)-4a,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-5-yloxy]-triisopropyl-silane