(3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene

Base Information

• Chemical Name: (3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene
• CAS No.: 119347-45-4
• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.434
• Mol file: 119347-45-4.mol

Synonyms:(3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene

Chemical Property of (3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene

There total 1 articles about (3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene 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: 13.4%

(3S,4aS,6RS,7RS,8aS)-3-acetoxyethyl-6,7-epoxy-2,2,6-trimethyl-1-methylene-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene (119347-46-5,119433-60-2) → (3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane (119347-47-6) + (3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene (119347-45-4)

Guidance literature:

With periodic acid; In tetrahydrofuran; diethyl ether; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90097-3

Reference yield: 86.7%

(3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene (119347-45-4) → (3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane (119347-47-6)

Guidance literature:

With lead(IV) acetate; sodium acetate; In benzene; Ambient temperature;

DOI:10.1016/S0040-4020(01)90097-3

Reference yield:

(3S,4aS,6S,7S,8aS)-3-acetoxyethyl-6,7-dihydroxy-2,2,6-trimethyl-1-methylenedecahydronaphthalene (119347-45-4) → (-)-khusimone (30557-76-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 86.7 percent / 90percent Pb(OAc)4, NaOAc / benzene / Ambient temperature

2: 81 percent / 10percent KOH / benzene / 1 h / Heating

3: 80 percent / pyridine / 6 h / Ambient temperature

4: 70 percent / NH₂OH*HCl, pyridine / ethanol / 6 h / Heating

5: 1.) MsCl, DMAP, pyridine 2.) 1N HCl / 1.) 0 to 5 deg C, 2.) 0 to 5 deg C, H₂O

6: 10percent aq. KOH / benzene / 1 h / Heating

7: 87.7 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - 0 °C

8: 98 percent / t-BuOK / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; lead(IV) acetate; hydrogenchloride; dmap; potassium hydroxide; hydroxylamine hydrochloride; potassium tert-butylate; sodium acetate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)90097-3

upstream raw materials:

(3S,4aS,6RS,7RS,8aS)-3-acetoxyethyl-6,7-epoxy-2,2,6-trimethyl-1-methylene-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene

Downstream raw materials:

(3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane

(-)-khusimone