Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

Base Information

• Chemical Name: Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate
• CAS No.: 229010-51-9
• Molecular Formula: C₂₁H₃₆O₄
• Molecular Weight: 352.514
• Mol file: 229010-51-9.mol

Synonyms:Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

Chemical Property of Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

There total 15 articles about Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate 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:

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0) → Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate (229010-51-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / K₂CO₃ / methanol

2: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

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

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

DOI:10.1039/a809983i

Reference yield:

(3R,4R)-3-Methyl-4-isopropenyl-3-vinylcyclohexanone (149404-72-8) → Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate (229010-51-9)

Guidance literature:

Multi-step reaction with 10 steps

1: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

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

3: 87 percent / imidazole / dimethylformamide / 1 h

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

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

6: Bu₄NF / tetrahydrofuran / 6 h

7: CrO₃, H₂SO₄, H₂O / acetone

8: diethyl ether / 0 °C

9: 98 percent / LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 to 0 deg C, 2 h, 2.) -78 deg C, 2 h

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

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

DOI:10.1039/a809983i

Reference yield:

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-4-<(5R)-2,2,4,4-tetramethyl-1,3-dioxolan-5-yl>butanoate (229010-50-8) → Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate (229010-51-9)

Guidance literature:

With water; pyridinium p-toluenesulfonate; In methanol; for 9h; Yield given; Heating;

DOI:10.1039/a809983i

upstream raw materials:

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-4-<(5R)-2,2,4,4-tetramethyl-1,3-dioxolan-5-yl>butanoate

(5R)-5-(2'-Iodoethyl)-2,2,4,4-tetramethyl-1,3-dioxolane

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene

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

Downstream raw materials:

lobatrientriol

lobatrienolide