(R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester
• CAS No.: 87322-20-1
• Molecular Formula: C₁₇H₂₈O₄
• Molecular Weight: 296.407
• Mol file: 87322-20-1.mol

Synonyms:(R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Chemical Property of (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

There total 21 articles about (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl 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: 83.5%

(R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester (87322-21-2) → (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester (87322-20-1)

Guidance literature:

With calcium carbonate; mercury dichloride; In water; acetonitrile; for 3h; Heating;

DOI:10.1016/S0040-4020(01)87487-1

Reference yield: 80.0%

(R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(E)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester (503272-16-0) → (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester (87322-20-1)

Guidance literature:

With calcium carbonate; mercury dichloride; In water; acetonitrile;

DOI:10.1016/S0040-4039(02)02500-5

Reference yield:

3-methyl-6-(prop-1-en-2-yl)cyclohexene (5113-87-1) → (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester (87322-20-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dicyclohexylborane / tetrahydrofuran / 168 h / 0 °C

1.2: 82 percent / H₂O₂; OH^(1-)

2.1: 80 percent / CrO₃; H₂SO₄ / acetone / 0 °C

3.1: KI; NaHCO₃ (aq.) / 48 h

4.1: 72 percent / (Me₃Si)3SiH; AIBN / toluene

5.1: BF₃*Et₂O / CH₂Cl₂ / 0 °C

6.1: NaOH (10 percent in MeOH) / Heating

7.1: diethyl ether

8.1: 89 percent / PCC / CH₂Cl₂ / 0 °C

9.1: 45 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 24 h / 50 °C

10.1: 80 percent / HgCl₂; CaCO₃ / acetonitrile; H₂O

With chromium(VI) oxide; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; sulfuric acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; potassium hexamethylsilazane; sodium hydrogencarbonate; pyridinium chlorochromate; calcium carbonate; potassium iodide; mercury dichloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 2.1: Jones oxidation;

DOI:10.1016/S0040-4039(02)02500-5

upstream raw materials:

(R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester

(R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(E)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester

3-methyl-6-(prop-1-en-2-yl)cyclohexene

(+)-(1R:4R)-trans-Δ²-p-Menthen-9-ol

Downstream raw materials:

arteannuin (Qinghaosu)

C₁₂H₁₃O₂(CH₃)3(O)(OO)