Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester

Base Information

• Chemical Name: Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester
• CAS No.: 131273-41-1
• Molecular Formula: C₁₃H₂₂O₄
• Molecular Weight: 242.315

Synonyms:Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester

Chemical Property of Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester

There total 7 articles about Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl 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:

(1R,4R,6R)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (35644-75-8,208397-90-4) → Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester (131273-41-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, -78 deg C,

2: 95 percent / (C₂H₅)3N, DMAP / CH₂Cl₂

3: 91 percent / L-selectride / tetrahydrofuran / -78 °C

4: 85 percent / (C₂H₅)3N / CH₂Cl₂ / 0 °C

5: 90 percent / NaC₁₀H₈ / tetrahydrofuran / Ambient temperature

6: 1.) n-C₄H₉Li / 1.) ether, hexane, 2.) 0 deg C

7: 90 percent / TBAF / tetrahydrofuran / Ambient temperature

With dmap; n-butyllithium; NaC₁₀H₈; tetrabutyl ammonium fluoride; L-Selectride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00002a043

Reference yield:

(R)-5-isopropyl-2-methylcyclohex-2-enone (33375-08-5) → Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester (131273-41-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / H₂O₂, NaOH / methanol

2: 1.) LDA / 1.) THF, -78 deg C,

3: 95 percent / (C₂H₅)3N, DMAP / CH₂Cl₂

4: 91 percent / L-selectride / tetrahydrofuran / -78 °C

5: 85 percent / (C₂H₅)3N / CH₂Cl₂ / 0 °C

6: 90 percent / NaC₁₀H₈ / tetrahydrofuran / Ambient temperature

7: 1.) n-C₄H₉Li / 1.) ether, hexane, 2.) 0 deg C

8: 90 percent / TBAF / tetrahydrofuran / Ambient temperature

With dmap; sodium hydroxide; n-butyllithium; NaC₁₀H₈; tetrabutyl ammonium fluoride; dihydrogen peroxide; L-Selectride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja00002a043

Reference yield:

(1R,3R,4S,6R)-3-Hydroxymethyl-4-isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (131250-59-4) → Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester (131273-41-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / (C₂H₅)3N, DMAP / CH₂Cl₂

2: 91 percent / L-selectride / tetrahydrofuran / -78 °C

3: 85 percent / (C₂H₅)3N / CH₂Cl₂ / 0 °C

4: 90 percent / NaC₁₀H₈ / tetrahydrofuran / Ambient temperature

5: 1.) n-C₄H₉Li / 1.) ether, hexane, 2.) 0 deg C

6: 90 percent / TBAF / tetrahydrofuran / Ambient temperature

With dmap; n-butyllithium; NaC₁₀H₈; tetrabutyl ammonium fluoride; L-Selectride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00002a043

upstream raw materials:

(1R,4R,6R)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

(R)-5-isopropyl-2-methylcyclohex-2-enone

(1R,3R,4S,6R)-3-Hydroxymethyl-4-isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

(1S,2S,3R,4S,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-ol

Downstream raw materials:

2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

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