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

Base Information

• Chemical Name: (1R,2S,4S,6R,8S,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-yl}-cyclohexanecarboxylic acid
• CAS No.: 652974-76-0
• Molecular Formula: C₂₅H₄₂O₆Si
• Molecular Weight: 466.69

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 2 articles about (1R,2S,4S,6R,8S,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-yl}-cyclohexanecarboxylic acid 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: 72.0%

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,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-cyclohexanecarboxylic acid (652974-76-0)

Guidance literature:

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; With potassium hexamethylsilazane; In toluene; at -78 ℃; for 1h;

With chloro-trimethyl-silane; diethylamine; In toluene; at -78 - 70 ℃; for 14h;

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,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-cyclohexanecarboxylic acid (652974-76-0)

Guidance literature:

Multi-step reaction with 2 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

With dmap; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene; 2.2: Ireland-Claisen rearrangement;

DOI:10.1016/j.tet.2003.10.062

Reference yield: 60.0%

(1R,2S,4S,6R,8S,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-cyclohexanecarboxylic acid (652974-76-0) → {1-[(1R,2S,4S,6R,8S,9R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl]-cyclohexyl}-methanol (652974-77-1)

Guidance literature:

(1R,2S,4S,6R,8S,9R)-1-{2-(diethylisopropylsilyloxy)-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-yl}-cyclohexanecarboxylic acid; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.666667h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 - -60 ℃; for 85.5h;

DOI:10.1016/j.tet.2003.10.062

upstream raw materials:

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

[(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

Downstream raw materials:

{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

(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

C₂₄H₄₀O₄Si

{(1S,3R,5S,7S,8R,9R,11R)-7-(diethylisopropylsilyloxy)-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxa-tetracyclo[6.3.1.0^3,70^9,11]dodec-9-yl}-methanol

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