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

Base Information

• Chemical Name: 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
• CAS No.: 652974-79-3
• Molecular Formula: C₂₅H₄₄O₄Si
• Molecular Weight: 436.707

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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: 87.0%

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

Guidance literature:

With sodium tetrahydroborate; In dimethyl sulfoxide; at 100 ℃; for 2h;

DOI:10.1016/j.tet.2003.10.062

Reference yield: 29.0%

{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,9S)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-79-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; methyltriphenoxyphosphonium iodide; sodium cyanoborohydride; at 100 ℃;

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,9S)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxatricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-79-3)

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

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; methyltriphenoxyphosphonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; 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:

{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

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

[(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,9R,10R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxa-10-oxirane-spiro-tricyclo[6.2.1.0^2,6]undec-9-yl}-1-methylcyclohexane

(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

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