3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid

Base Information

• Chemical Name: 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid
• CAS No.: 1373344-38-7
• Molecular Formula: C₁₆H₃₀O₄Si
• Molecular Weight: 314.497

Synonyms:3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid

Chemical Property of 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid

Chemical Property:

Purity/Quality:

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Technology Process of 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid

There total 4 articles about 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid 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: 88.0%

(4aS,5S)-4a-methyl-5-((triethylsilyl)oxy)-4,4,5,6,7,8-hexahydronaphthalen-2(3H)-one (1373344-35-4) → 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid (1373344-38-7)

Guidance literature:

With ozone; In methanol; at -78 ℃; for 0.833333h;

DOI:10.1021/acs.joc.6b02264

Reference yield:

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) → 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid (1373344-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 12 h / 20 °C

2: ozone / methanol / 2 h / -78 °C

With 1H-imidazole; ozone; In methanol; dichloromethane;

DOI:10.1135/cccc2011039

Reference yield:

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → 3-((1R,6S)-1-methyl-2-oxo-6-((triethylsilyl)oxy)cyclohexyl)propanoic acid (1373344-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate; (R,R)-TADDOL / methanol; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 12 h / 20 °C

3: ozone / methanol / 2 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; (R,R)-TADDOL; ozone; In methanol; dichloromethane;

DOI:10.1135/cccc2011039

upstream raw materials:

(4aS,5S)-4a-methyl-5-((triethylsilyl)oxy)-4,4,5,6,7,8-hexahydronaphthalen-2(3H)-one

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

Wieland-Miescher ketone

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Downstream raw materials:

(4aR,8aS)-4a-methylhexahydrochromene-2-one-5-N'-(2,4,6-triisopropylbenzenesulfono)hydrazone

2,4,6-triisopropyl-N′-((2S,4S,8S)-2-methoxy-4-methyloctahydro-5H-chromen-5-ylidene)benzenesulfonohydrazide

1-((2S,4aS,8aS)-2-methoxy-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-chromen-5-yl)-3-phenylpropan-1-ol

(2R,4aR,8aS)-4a-methyl-2-trityloxyoctahydrochromen-5-N'-(2,4,6-triisopropylbenzenesulfono)hydrazone

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