methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate
• CAS No.: 104112-12-1
• Molecular Formula: C₁₁H₁₈O₃
• Molecular Weight: 198.262
• Mol file: 104112-12-1.mol

Synonyms:methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

Chemical Property of methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

There total 5 articles about methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate 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: 95.0%

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate (28120-76-5) → methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (104112-12-1)

Guidance literature:

With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jacs.6b12654

Reference yield:

methyl 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (91029-31-1) → methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (104112-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dipyridinium dichromate / dichloromethane / 2 h / 0 - 25 °C

2: borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C

With dipyridinium dichromate; borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jacs.6b12654

Reference yield:

(R)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5) → methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (104112-12-1)

Guidance literature:

In water; at 37 ℃; for 10h; β-glucosidase;

DOI:10.1248/cpb.44.41

upstream raw materials:

(R)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester

(3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid

methyl 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate

Downstream raw materials:

Benzoic acid (R)-3-methoxycarbonyl-2,4,4-trimethyl-cyclohex-2-enyl ester

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate

methyl 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

3-Methoxy-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid