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

Base Information

• Chemical Name: (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
• CAS No.: 636599-74-1
• Molecular Formula: C₂₀H₂₈O₂S
• Molecular Weight: 332.507

Synonyms:(1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

Chemical Property of (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

There total 4 articles about (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-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: 85.0%

ethylmagnesium bromide (925-90-6) + (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (599192-45-7) → (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (636599-74-1)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1016/j.tetasy.2003.07.017

Reference yield:

2,2-diethoxyacetophenone (6175-45-7) → (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (636599-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / p-TsOH / toluene / 0.75 h / Heating

2: 85 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

With toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/j.tetasy.2003.07.017

Reference yield:

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol (444308-38-7) → (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (636599-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / p-TsOH / toluene / 0.75 h / Heating

2: 85 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

With toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/j.tetasy.2003.07.017

upstream raw materials:

ethylmagnesium bromide

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

2,2-diethoxyacetophenone

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol

Downstream raw materials:

(S)-(-)-hydroxy-2-phenylbutanal

(1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide

(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

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