(1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

Base Information

• Chemical Name: (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
• CAS No.: 444308-42-3
• Molecular Formula: C₁₉H₂₆O₂S
• Molecular Weight: 318.48
• Mol file: 444308-42-3.mol

Synonyms:(1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

Chemical Property of (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

There total 9 articles about (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 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: 92.0%

phenylmagnesium bromide + (1S,2R,5R,7S)-5-acetyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-41-2) → (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-42-3)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(01)00545-6

Reference yield: 89.0%

phenyllithium (591-51-5) + (1S,2R,5R,7S)-5-acetyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-41-2) → (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-42-3)

Guidance literature:

In tetrahydrofuran; cyclohexane; at -78 ℃; for 2h;

DOI:10.1016/S0957-4166(01)00545-6

Reference yield:

myrtenal (564-94-3,18486-69-6) → (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / DBU

2.1: 90 percent / LiAlH₄ / diethyl ether

3.1: 30 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating

4.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.67 h / -78 °C

4.2: tetrahydrofuran; cyclohexane / 2 h

With lithium aluminium tetrahydride; sec.-butyllithium; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; cyclohexane; benzene;

DOI:10.1021/jo034404w

upstream raw materials:

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

phenyllithium

acetophenone

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

Downstream raw materials:

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

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

(1S,2R,3S,5R,1'R,2'S)-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,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