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

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}-1-iodomethyl-cyclohexane
• CAS No.: 652974-78-2
• Molecular Formula: C₂₅H₄₃IO₄Si
• Molecular Weight: 562.604

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}-1-iodomethyl-cyclohexane

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}-1-iodomethyl-cyclohexane

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}-1-iodomethyl-cyclohexane

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}-1-iodomethyl-cyclohexane 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: 93.0%

{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) → 1-{(1R,2S,4S,6R,8S,9R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-1-iodomethyl-cyclohexane (652974-78-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 23 ℃; for 11h;

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}-1-iodomethyl-cyclohexane (652974-78-2)

Guidance literature:

Multi-step reaction with 5 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: 93 percent / I₂; imidazole; PPh₃ / benzene / 11 h / 23 °C

With 1H-imidazole; dmap; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In diethyl ether; dichloromethane; toluene; benzene; 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) → 1-{(1R,2S,4S,6R,8S,9R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-1-iodomethyl-cyclohexane (652974-78-2)

Guidance literature:

Multi-step reaction with 4 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: 93 percent / I₂; imidazole; PPh₃ / benzene / 11 h / 23 °C

With 1H-imidazole; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triphenylphosphine; In diethyl ether; dichloromethane; toluene; benzene; 1.2: Ireland-Claisen rearrangement;

DOI:10.1016/j.tet.2003.10.062

upstream 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)-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

(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

Downstream raw materials:

(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

{(1R,2S,4S,6R,8S)-2-(diethylisopropylsilyloxy)-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-yl}-methanol

(1S,2S,4S,6R,8S,9R,10R)-10-bromo-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.0^2,6]undecane-10-carbaldehyde

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