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

Base Information

• Chemical Name: 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
• CAS No.: 163015-25-6
• Molecular Formula: C₁₃H₂₀O₄
• Molecular Weight: 240.299

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 1 articles about 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 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: 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:

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) → (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 7 steps

1: 70 percent / O₃ / CH₂Cl₂ / -78 °C

2: 92 percent / imidazole / DMAP / CH₂Cl₂

3: 84 percent / L-Selectride / tetrahydrofuran / -78 °C

4: 90 percent / 1percent HCl / ethanol

5: 94 percent / pyridinium toluene-p-sulfonate / toluene / Heating

6: 72 percent / DIBAH / toluene / -78 deg C to r.t.

7: 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

Reference yield:

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) → ((1S,2S,6R,7R,8S,9R)-9-Benzyloxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]dec-8-yl)-methanol (163015-30-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / O₃ / CH₂Cl₂ / -78 °C

2: 92 percent / imidazole / DMAP / CH₂Cl₂

3: 84 percent / L-Selectride / tetrahydrofuran / -78 °C

4: 90 percent / 1percent HCl / ethanol

5: 94 percent / pyridinium toluene-p-sulfonate / toluene / Heating

6: 72 percent / DIBAH / toluene / -78 deg C to r.t.

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

DOI:10.1039/c39950000453

upstream raw materials:

(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

Downstream raw materials:

(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

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