(1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester

Base Information

• Chemical Name: (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester
• CAS No.: 117065-50-6
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.307
• Mol file: 117065-50-6.mol

Synonyms:(1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester

Chemical Property of (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester

There total 1 articles about (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester 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: 87.0%

lithium benzyloxide (15082-42-5) + <1S-<1α(R*),6β>>-3-<(6-methyl-3-cyclohexen-1-yl)carbonyl>-4-(phenylmethyl)-2-oxazolidinone (116996-49-7) → (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester (117065-50-6)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1021/ja00164a024

Reference yield: 87.0%

lithium methanolate (865-34-9) + (1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester (117065-50-6) → methyl (1S,6S)-6-methylcyclohex-3-ene-1-carboxylate (117065-51-7)

Guidance literature:

In methanol; dichloromethane; for 46h; Heating;

DOI:10.1021/ja00164a024

Reference yield:

(1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester (117065-50-6) → <1S-<1α,4α-(4S*,6R*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one (116996-30-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / methanol; CH₂Cl₂ / 46 h / Heating

2: 1.) LDA, 2.) CH₃COOH / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C

3: 99 percent / LiAlH₄ / tetrahydrofuran / 15 h / Heating

4: 90 percent / pyridine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

5: 92 percent / dimethylsulfoxide / 10 h / 75 °C

6: 92 percent / aq. NaOH / 24 h / Heating

7: 91 percent / NaI, 18-crown-6, m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

8: 79 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 2 h / Heating

9: 1.) LDA / 1.) THF, -78 deg C, 1.25 h, 2.) THF, hexamethylphosphoric triamide (HMPA), from -78 deg C to RT, overnight

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; 18-crown-6 ether; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/ja00164a024

upstream raw materials:

lithium benzyloxide

<1S-<1α(R^*),6β>>-3-<(6-methyl-3-cyclohexen-1-yl)carbonyl>-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

methyl (1S,6S)-6-methylcyclohex-3-ene-1-carboxylate

5r-Methyl-4c-methoxycarbonylcyclohex-1-en

(1R,6S)-6-methyl-3-cyclohexenemethanol

((1S,6S)-6-Methyl-cyclohex-3-enyl)-acetonitrile