(1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate

Base Information

• Chemical Name: (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate
• CAS No.: 1373344-44-5
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 1373344-44-5.mol

Synonyms:

Chemical Property of (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate

There total 4 articles about (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate 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:

(+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one (32042-79-8,93903-43-6,126452-85-5,110715-79-2) → (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate (1373344-44-5)

Guidance literature:

With ozone; In methanol; at -78 ℃; for 2h;

DOI:10.1135/cccc2011039

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) → (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate (1373344-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / dichloromethane / 12 h / 0 °C

2: ozone / methanol / 2 h / -78 °C

With pyridine; dmap; 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) → (1S,2R)-2-(2-carboxyethyl)-2-methyl-3-oxocyclohexyl benzoate (1373344-44-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine; dmap / dichloromethane / 12 h / 0 °C

3: ozone / methanol / 2 h / -78 °C

With pyridine; dmap; sodium tetrahydroborate; (R,R)-TADDOL; ozone; In methanol; dichloromethane;

DOI:10.1135/cccc2011039

upstream raw materials:

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

Wieland-Miescher ketone

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

benzoyl chloride

Downstream raw materials:

(1S,2R)-2-(2-methoxycarbonylethyl)-2-methyl-3-oxocyclohexyl benzoate

(1S,2R)-2-(2-methoxycarbonylethyl)-2-methyl-3-benzoylcyclohexyl-N'-(2,4,6-triisopropylbenzenesulfono)hydrazone

(2S,4aR,8aS)-2-hydroxy-4a-methyloctahydrochromen-5-N'-(2,4,6-triisopropylbenzenesulfono)hydrazone

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

Refernces