(1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol

Base Information

• Chemical Name: (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol
• CAS No.: 652974-80-6
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418

Synonyms:(1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol

Chemical Property of (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol

There total 7 articles about (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-2-ol 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: 100.0%

1-{(1R,2S,4S,6R,8S,9S)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-79-3) → (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.02,6]undecan-2-ol (652974-80-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.666667h;

DOI:10.1016/j.tet.2003.10.062

Reference yield:

[(1R,2S,4S,6R,8S)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.02,6]undec-9-en-10-yl]-methanol (223786-94-5) → (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.02,6]undecan-2-ol (652974-80-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMAP; EDCI*HCl / CH₂Cl₂ / 0.25 h

1.2: 92 percent / CH₂Cl₂ / 2 h / 23 °C

2.1: KHMDS / toluene / 1 h / -78 °C

2.2: 72 percent / TMSCl; Et₂N / toluene / 14 h / -78 - 70 °C

3.1: diethyl ether / 0.5 h / 0 °C

4.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

5.1: 29 percent / MeP(OPh)3I; NaBH₃CN; HMPA / 100 °C

6.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.67 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.2: Ireland-Claisen rearrangement;

DOI:10.1016/j.tet.2003.10.062

Reference yield:

cyclohexanecarboxylic acid (1R,2S,4S,6R,8S)-2-(diethylisopropylsilyloxy)-4-methoxy-5,7-dioxatricyclo[6.2.1.02,6]undec-9-en-10-ylmethyl ester (652974-75-9) → (1R,2S,4S,6R,8S,9S)-4-Methoxy-9-(1-methyl-cyclohexyl)-10-methylene-5,7-dioxa-tricyclo[6.2.1.02,6]undecan-2-ol (652974-80-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KHMDS / toluene / 1 h / -78 °C

1.2: 72 percent / TMSCl; Et₂N / toluene / 14 h / -78 - 70 °C

2.1: diethyl ether / 0.5 h / 0 °C

3.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: 29 percent / MeP(OPh)3I; NaBH₃CN; HMPA / 100 °C

5.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.67 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.2: Ireland-Claisen rearrangement;

DOI:10.1016/j.tet.2003.10.062

upstream raw materials:

1-{(1R,2S,4S,6R,8S,9S)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-yl}-1-methylcyclohexane

[(1R,2S,4S,6R,8S)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-yl]-methanol

cyclohexanecarboxylic acid (1R,2S,4S,6R,8S)-2-(diethylisopropylsilyloxy)-4-methoxy-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-en-10-ylmethyl ester

{1-[(1R,2S,4S,6R,8S,9R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-yl]-cyclohexyl}-methanol

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