{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

Base Information

• Chemical Name: {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
• CAS No.: 652974-77-1
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707

Synonyms:{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

Chemical Property of {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

Chemical Property:

Purity/Quality:

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Technology Process of {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

There total 4 articles about {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 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: 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

Reference yield:

1-[(1R,2S,4S,6R,8S,9R)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-10-methylene-5,7-dioxa-tricyclo[6.2.1.02,6]undec-9-yl]-cyclohexanecarboxylic acid methyl ester → {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:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;

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) → {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:

Multi-step reaction with 4 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

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

DOI:10.1016/j.tet.2003.10.062

upstream raw materials:

(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

[(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

Downstream 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

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}-1-iodomethyl-cyclohexane

(1S,3R,5S,7S,8R,9S,11R)-7-(diethylisopropylsilyloxy)-9-iodomethyl-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxatetracyclo[6.3.1.0^3,70^9,11]dodecane

{(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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