(1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one

Base Information

• Chemical Name: (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one
• CAS No.: 108147-34-8
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 108147-34-8.mol

Synonyms:(1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one

Chemical Property of (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one

There total 13 articles about (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one 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:

3-hydroxy acetal silyl ether → (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one (108147-34-8)

Guidance literature:

With sulfuric acid; In acetonitrile; at 23 ℃; for 16h; Yield given;

DOI:10.1021/jo00389a038

Reference yield:

1-cyclohexylprop-2-yn-1-ol (97563-45-6,105880-38-4,128241-52-1,4187-88-6) → (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one (108147-34-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C

2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

3: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

5: 35.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

6: LiAlH₄ / tetrahydrofuran / 1 h / Heating

7: 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

With chromium(VI) oxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00389a038

Reference yield:

cyclohexanecarbaldehyde (2043-61-0) → (1S,2R,3S,6R)-2-((S)-3-Cyclohexyl-3-hydroxy-prop-1-ynyl)-3-hydroxy-bicyclo[4.2.0]octan-7-one (108147-34-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) ethylmagnesium bromide / 1.) THF, 2.) THF, 23 deg C, 16 h

2: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C

3: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

4: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

5: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

6: 35.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

7: LiAlH₄ / tetrahydrofuran / 1 h / Heating

8: 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

With chromium(VI) oxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; ethylmagnesium bromide; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00389a038

upstream raw materials:

1-cyclohexylprop-2-yn-1-ol

1-cyclohexyl-2-propyn-1-one

bicyclo[4.2.0]-oct-2-en-7-one

(3S)-3-(tert-butyldimethyl-siloxy)-3-cyclohexylprop-1-yne

Downstream raw materials:

RS₉₃₅₂₀