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

Base Information

• Chemical Name: 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
• CAS No.: 652974-82-8
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 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

There total 5 articles about 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 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: 90.0%

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) → 1-{(1R,2S,4S,6R,8S,9R,10R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxa-10-oxirane-spiro-tricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-82-8)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 23 ℃; for 18h;

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,10R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxa-10-oxirane-spiro-tricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-82-8)

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: 90 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 18 h / 23 °C

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

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,10R)-2-diethylisopropylsilyloxy-4-methoxy-10-methylidene-5,7-dioxa-10-oxirane-spiro-tricyclo[6.2.1.02,6]undec-9-yl}-1-methylcyclohexane (652974-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2: 29 percent / MeP(OPh)3I; NaBH₃CN; HMPA / 100 °C

3: 90 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 18 h / 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; methyltriphenoxyphosphonium iodide; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

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

{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

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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