(1S,2S,6R,7R,8S)-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,8S)-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.: 120424-44-4
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499

Synonyms:(1S,2S,6R,7R,8S)-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,8S)-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

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Technology Process of (1S,2S,6R,7R,8S)-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 14 articles about (1S,2S,6R,7R,8S)-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: 92.0%

(-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)bicyclo-<2.2.1>hept-2-ene-2-carboxylate (110550-21-5) → (-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)bicyclo<2.2.1>heptane-2-α/β-carboxylate (120424-44-4,120521-58-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; under 1 Torr;

Reference yield:

(-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)bicyclo-<2.2.1>hept-2-ene-2-carboxylate (110550-21-5) → (1S,2S,6R,7R,8S)-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 (120424-44-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; under 1 Torr;

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propiolate (65018-52-2) → (-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)bicyclo<2.2.1>heptane-2-α/β-carboxylate (120424-44-4,120521-58-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Et₃N / dimethylsulfoxide; CH₂Cl₂ / -75 deg C, addition, then to -30 deg C, 1 h

2: 23 percent / MCPBA / CH₂Cl₂ / addition, -70 deg C, then to 0 deg C, 3 h

3: 1.) Et₂AlCl(hexane) / 1.) CH₂Cl₂, -70 deg C, 5 min, then, 15 min, 2.) CH₂Cl₂, -70 deg C, 3 h

4: 1.) OsO₄, Et₃NO*2H₂O / 2.) TSA / 1.) t-BuOH, acetone, water, 3 h, room t., 2.) acetone, 3 h, reflux

5: MCPBA / CH₂Cl₂ / 1 h / Ambient temperature

6: 67 percent / DBU / dimethylsulfoxide / 4 h / 55 °C

7: 92 percent / H₂ / 10 percent Pd-C / ethanol / 4 h / 1 Torr

With osmium(VIII) oxide; triethylamine N-oxide; hydrogen; diethylaluminium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

(-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)bicyclo-<2.2.1>hept-2-ene-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propiolate

(Z)-3-(Pyridin-2-ylsulfanyl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(S_S)(Z)-menthyl 3-(2-pyridylsulphinyl)acylate

Downstream raw materials:

(1R,2R/S,5R,6R,7S)-6,7-Isopropylidenedioxy-3-oxabicyclo[3.2.1]octan-2-ol

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