(1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: (1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 163015-24-5
• Molecular Formula: C₃₃H₅₂O₆
• Molecular Weight: 544.772
• Mol file: 163015-24-5.mol

Synonyms:(1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property of (1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

There total 1 articles about (1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 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: 98.0%

acetone (67-64-1) + (1R,2R,4S,5S,6R)-5,6-Dihydroxy-3-[1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (163015-23-4) → (1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (163015-24-5)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate;

DOI:10.1039/c39950000453

Reference yield: 96.0%

(1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (163015-24-5) → (-)-menthol (2216-51-5) + 2-[(1R,2R,6S,7S,9R)-9-Hydroxymethyl-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]dec-(8E)-ylidene]-ethanol (163015-25-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1039/c39950000453

Reference yield:

(1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (163015-24-5) → (1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol (163015-31-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / DIBAH / CH₂Cl₂ / -78 - 0 °C

2: 70 percent / O₃ / CH₂Cl₂ / -78 °C

3: 92 percent / imidazole / DMAP / CH₂Cl₂

4: 84 percent / L-Selectride / tetrahydrofuran / -78 °C

5: 90 percent / 1percent HCl / ethanol

6: 94 percent / pyridinium toluene-p-sulfonate / toluene / Heating

7: 72 percent / DIBAH / toluene / -78 deg C to r.t.

8: 71 percent / 2 M HCl / 1,2-dimethoxy-ethane / 80 °C

With 1H-imidazole; hydrogenchloride; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; ozone; dmap; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene;

DOI:10.1039/c39950000453

upstream raw materials:

acetone

(1R,2R,4S,5S,6R)-5,6-Dihydroxy-3-[1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Downstream raw materials:

(-)-menthol

2-[(1R,2R,6S,7S,9R)-9-Hydroxymethyl-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-(8E)-ylidene]-ethanol

(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

((1S,2S,6R,7R,8S,9R)-9-Benzyloxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-8-yl)-methanol