(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

Base Information

• Chemical Name: (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
• CAS No.: 682352-10-9
• Molecular Formula: C₂₆H₄₂O₃SSi
• Molecular Weight: 462.769
• Mol file: 682352-10-9.mol

Synonyms:(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

Chemical Property of (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

There total 19 articles about (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane (682352-08-5) → (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-10-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetasy.2005.03.032

Reference yield:

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol (444308-38-7) → (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-toluenesulfonic acid / CH₂Cl₂ / 5 h / 20 °C

1.2: 0.6 g / potassium carbonate / tetrahydrofuran / 24 h / 20 °C

2.1: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1016/j.tetasy.2005.03.032

Reference yield:

2,2-diethoxyacetophenone (6175-45-7) → (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane (682352-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-toluenesulfonic acid / CH₂Cl₂ / 5 h / 20 °C

1.2: 0.6 g / potassium carbonate / tetrahydrofuran / 24 h / 20 °C

2.1: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1016/j.tetasy.2005.03.032

upstream raw materials:

tert-butyldimethylsilyl chloride

(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane

(1S,2R,5R,7S,9R)-5-propionyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

(1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.0^2,7]undecane

Downstream raw materials:

bis-[(1S,2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl] disulfide

(S)-2-Phenyl-hexane-1,2-diol

(1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane

(1S,2R)-1-[(1S,2R,3S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylsulfanyl]-1-ethoxy-3-methyl-2-phenyl-butan-2-ol