(1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

Base Information

• Chemical Name: (1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester
• CAS No.: 229010-41-7
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401
• Mol file: 229010-41-7.mol

Synonyms:(1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

Chemical Property of (1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

There total 1 articles about (1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl 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: 95.0%

bromoacetic acid methyl ester (96-32-2) + (1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester (202194-28-3) → (1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester (229010-41-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 30 min, 2.) 0 deg c to r.t., 4 h;

DOI:10.1039/a809983i

Reference yield:

(1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester (229010-41-7) → ((1S,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexyl)-acetic acid

Guidance literature:

With sodium hydroxide; water; In dimethyl sulfoxide; at 50 ℃; for 12h;

DOI:10.1039/a809983i

Reference yield:

(1S,4R,5R)-5-Isopropenyl-1-methoxycarbonylmethyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester (229010-41-7) → lobatrientriol (139579-30-9)

Guidance literature:

Multi-step reaction with 15 steps

1: NaOH, H₂O / dimethylsulfoxide / 12 h / 50 °C

2: diethyl ether / 0 °C

3: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

4: 87 percent / imidazole / dimethylformamide / 1 h

5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

6: AIBN, HSnBu₃ / toluene / 0.5 h / 90 °C

7: Bu₄NF / tetrahydrofuran / 6 h

8: CrO₃, H₂SO₄, H₂O / acetone

9: diethyl ether / 0 °C

10: 98 percent / LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 to 0 deg C, 2 h, 2.) -78 deg C, 2 h

11: PPTS, H₂O / methanol / 9 h / Heating

12: 80 percent / p-TsOH / CH₂Cl₂ / 8 h / Heating

13: 63 percent / LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 to -30 deg C, 3 h

14: 70 percent / H₂O₂, H₂O / tetrahydrofuran / 12 h / 0 °C

15: 11 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

With 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/a809983i

upstream raw materials:

bromoacetic acid methyl ester

(1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

Downstream raw materials:

lobatrientriol

lobatrienolide

2-<(1S,3R,4R)-(3-Isopropenyl-4-methyl-4-vinylcyclohexyl)>ethanol

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate