(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

Base Information

• Chemical Name: (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
• CAS No.: 652974-95-3
• Molecular Formula: C₂₅H₄₃IO₅Si
• Molecular Weight: 578.603

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (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

There total 8 articles about (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 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: 82.0%

{(1S,3R,5S,7S,8R,9R,11R)-7-(diethylisopropylsilyloxy)-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxa-tetracyclo[6.3.1.03,709,11]dodec-9-yl}-methanol (652974-93-1) → (1S,3R,5S,7S,8R,9S,11R)-7-(diethylisopropylsilyloxy)-9-iodomethyl-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxatetracyclo[6.3.1.03,709,11]dodecane (652974-95-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 23 ℃; for 8h;

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) → (1S,3R,5S,7S,8R,9S,11R)-7-(diethylisopropylsilyloxy)-9-iodomethyl-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxatetracyclo[6.3.1.03,709,11]dodecane (652974-95-3)

Guidance literature:

Multi-step reaction with 12 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

10.1: 78 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C

11.1: 100 percent / VO(acac)2; TBHP / CH₂Cl₂ / 0 - 23 °C

12.1: 82 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 8 h / 23 °C

With 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; methyltriphenoxyphosphonium iodide; iodine; lithium carbonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: Ireland-Claisen rearrangement / 10.1: Luche reduction;

DOI:10.1016/j.tet.2003.10.062

Reference yield:

(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) → (1S,3R,5S,7S,8R,9S,11R)-7-(diethylisopropylsilyloxy)-9-iodomethyl-5-methoxy-11-(1-methylcyclohexyl)-2,4,10-trioxatetracyclo[6.3.1.03,709,11]dodecane (652974-95-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diethyl ether / 0.5 h / 0 °C

2.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

3.1: 29 percent / MeP(OPh)3I; NaBH₃CN; HMPA / 100 °C

4.1: 90 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 18 h / 23 °C

5.1: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 7 h / -55 °C

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

6.2: 71 percent / NBS / tetrahydrofuran; toluene / 2 h / -60 °C

7.1: 97 percent / LiBr; Li₂CO₃ / dimethylformamide / 13 h / 125 °C

8.1: 78 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C

9.1: 100 percent / VO(acac)2; TBHP / CH₂Cl₂ / 0 - 23 °C

10.1: 82 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 8 h / 23 °C

With 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; methyltriphenoxyphosphonium iodide; iodine; lithium carbonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: Luche reduction;

DOI:10.1016/j.tet.2003.10.062

upstream raw materials:

{(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-(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:

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

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