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

Base Information

• Chemical Name: (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-ene-10-carbaldehyde
• CAS No.: 652974-88-4
• Molecular Formula: C₂₅H₄₂O₅Si
• Molecular Weight: 450.691

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

Chemical Property of (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-ene-10-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-ene-10-carbaldehyde

There total 7 articles about (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.0^2,6]undec-9-ene-10-carbaldehyde 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: 97.0%

(1S,2S,4S,6R,8S,9R,10R)-10-bromo-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.02,6]undecane-10-carbaldehyde (652974-85-1) → (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.02,6]undec-9-ene-10-carbaldehyde (652974-88-4)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 125 ℃; for 13h;

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)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.02,6]undec-9-ene-10-carbaldehyde (652974-88-4)

Guidance literature:

Multi-step reaction with 9 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

7.1: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 7 h / -55 °C

8.1: KHMDS; HMPA / tetrahydrofuran; toluene / 0.33 h / -60 °C

8.2: 71 percent / NBS / tetrahydrofuran; toluene / 2 h / -60 °C

9.1: 97 percent / LiBr; Li₂CO₃ / dimethylformamide / 13 h / 125 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; boron trifluoride diethyl etherate; methyltriphenoxyphosphonium iodide; lithium carbonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 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 → (1R,2S,4S,6R,8S)-2-diethylisopropylsilyloxy-4-methoxy-9-(1-methylcyclohexyl)-5,7-dioxatricyclo[6.2.1.02,6]undec-9-ene-10-carbaldehyde (652974-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2.1: 29 percent / MeP(OPh)3I; NaBH₃CN; HMPA / 100 °C

3.1: 90 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 18 h / 23 °C

4.1: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 7 h / -55 °C

5.1: KHMDS; HMPA / tetrahydrofuran; toluene / 0.33 h / -60 °C

5.2: 71 percent / NBS / tetrahydrofuran; toluene / 2 h / -60 °C

6.1: 97 percent / LiBr; Li₂CO₃ / dimethylformamide / 13 h / 125 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; boron trifluoride diethyl etherate; methyltriphenoxyphosphonium iodide; lithium carbonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2003.10.062

upstream raw materials:

(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

[(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,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

{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

Downstream raw materials:

{(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

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