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

Base Information

• Chemical Name: (3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane
• CAS No.: 119347-47-6
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 119347-47-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane 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: 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: 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:

(S)-5-methoxycarbonylmethyl-6,6-dimethyl-2-cyclohexen-1-one (70591-46-7) → (3S,5R,6S)-3-acetoxy-5-(2-oxopropyl)-6-formylmethyl-2,2-dimethyl-1-methylenecyclohexane (119347-47-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) SnCl₄ / 1.) CH₂Cl₂, 20 to 25 deg C, 5 h, 2.) CH₂Cl₂, 48 h, RT; var. solv., time, temp. and cat.: AlCl₃, BF₃*Et₂O

2: 95 percent / NaOMe / methanol / 3 h / Ambient temperature

3: 75 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) RT

4: 78 percent / Li, NH₃ / tetrahydrofuran / 1 h / -23 °C

5: 92 percent / LAH / diethyl ether / 0.5 h / Heating

6: 95 percent / pyridine / Ambient temperature

7: 85 percent / 80percent MCPBA / CHCl₃ / 0 - 5 °C

8: 85.5 percent / HIO₄ / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; ammonia; sodium methylate; lithium; periodic acid; 3-chloro-benzenecarboperoxoic acid; tin(IV) chloride; In tetrahydrofuran; methanol; diethyl ether; chloroform;

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

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

(S)-5-methoxycarbonylmethyl-6,6-dimethyl-2-cyclohexen-1-one

(3S,4aS,8aS)-3-hydroxyethyl-2,2,6-trimethyl-1-methylene-1,2,3,4,4a,5,8,8a-octahydronaphthalene

Downstream raw materials:

(-)-khusimone