(1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone

Base Information

• Chemical Name: (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone
• CAS No.: 119371-64-1
• Molecular Formula: C₂₂H₂₈O₂S
• Molecular Weight: 356.529
• Mol file: 119371-64-1.mol

Synonyms:

Chemical Property of (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone

There total 4 articles about (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone 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: 75.0%

(phenylthio)methyllithium (13307-75-0) + (3S,4aS,8aS)-3,4,4a,5,8,8a-hexahydro-3-methoxycarbonylmethyl-2,2,6-trimethyl-1(2H)-naphthalenone (119371-62-9) → (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone (119371-64-1)

Guidance literature:

In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) RT;

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

Reference yield:

ammonium salt of (-)-10-camphorsulfonic acid (14888-09-6,82509-30-6,83846-91-7) → (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone (119371-64-1)

Guidance literature:

Multi-step reaction with 4 steps

2: 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

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

4: 75 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) RT

With sodium methylate; tin(IV) chloride; In tetrahydrofuran; methanol;

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

Reference yield:

(S)-5-methoxycarbonylmethyl-6,6-dimethyl-2-cyclohexen-1-one (70591-46-7) → (1S,3S,4aS,8aS)-1-hydroxy-1-phenylthiomethyl-2,2,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-3-ylacetic acid δ-lactone (119371-64-1)

Guidance literature:

Multi-step reaction with 3 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

With sodium methylate; tin(IV) chloride; In tetrahydrofuran; methanol;

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

upstream raw materials:

(phenylthio)methyllithium

(3S,4aS,8aS)-3,4,4a,5,8,8a-hexahydro-3-methoxycarbonylmethyl-2,2,6-trimethyl-1(2H)-naphthalenone

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

ammonium salt of (-)-10-camphorsulfonic acid

Downstream raw materials:

(-)-khusimone

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