3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

Base Information

• Chemical Name: 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde
• CAS No.: 125975-01-1
• Molecular Formula: C₃₄H₄₈O₅Si
• Molecular Weight: 564.838
• Mol file: 125975-01-1.mol

Synonyms:

Chemical Property of 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

There total 19 articles about 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-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: 90.0%

<1S-<1α,4α-(4S*,6R*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one (116996-30-6) → 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde (125975-01-1,126060-28-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/ja00164a024

Reference yield:

4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one (116996-55-5,126060-84-2) → 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde (125975-01-1,126060-28-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.72 g / TsOH*H₂O / acetone / 91 h / Ambient temperature

2: 85 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 1.) LDA / 1.) THF, -78 deg C, 1.25 h, 2.) THF, hexamethylphosphoric triamide (HMPA), from -78 deg C to RT, overnight

4: 90 percent / 1 M diisobutylaluminium hydride / CH₂Cl₂ / 1.5 h / -78 °C

With dmap; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In dichloromethane; acetone;

DOI:10.1021/ja00164a024

Reference yield:

(3R)-1-(tert-butyldiphenylsilyloxy)hex-5-en-3-ol (112897-09-3) → 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde (125975-01-1,126060-28-4)

Guidance literature:

Multi-step reaction with 5 steps

2: 2.72 g / TsOH*H₂O / acetone / 91 h / Ambient temperature

3: 85 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 1.) LDA / 1.) THF, -78 deg C, 1.25 h, 2.) THF, hexamethylphosphoric triamide (HMPA), from -78 deg C to RT, overnight

5: 90 percent / 1 M diisobutylaluminium hydride / CH₂Cl₂ / 1.5 h / -78 °C

With dmap; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In dichloromethane; acetone;

DOI:10.1021/ja00164a024

upstream raw materials:

<1S-<1α,4α-(4S^*,6R^*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one

5r-Methyl-4c-methoxycarbonylcyclohex-1-en

(1R,6S)-6-methyl-3-cyclohexenemethanol

((1S,6S)-6-Methyl-cyclohex-3-enyl)-acetonitrile