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

Base Information

• Chemical Name: (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
• CAS No.: 599192-45-7
• Molecular Formula: C₁₈H₂₂O₂S
• Molecular Weight: 302.437

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

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

Chemical Property:

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

There total 8 articles about (1S,2R,5R,7S,9R)-5-benzoyl-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: 78.0%

(1S,2R,3S,5R)-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-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (599192-45-7)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 1h; Heating;

DOI:10.1016/j.tetlet.2004.01.046

Reference yield: 30.0%

benzonitrile (100-47-0) + (1S,2R,7S)-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (444308-39-8) → (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (599192-45-7)

Guidance literature:

(1S,2R,7S)-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.666667h;

benzonitrile; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.75h;

DOI:10.1021/jo034404w

Reference yield:

myrtenal (564-94-3,18486-69-6) → (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane (599192-45-7)

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: 30 percent / tetrahydrofuran; cyclohexane / 0.75 h / -78 °C

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:

benzonitrile

(1S,2R,7S)-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:

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

(1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1',3'-diphenyl-2'-propyn-1'-yl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane

(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

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

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