(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
Hs Code.:

Synonyms:

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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

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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%

: 13307-75-0
(phenylthio)methyllithium

: 119371-62-9
(3S,4aS,8aS)-3,4,4a,5,8,8a-hexahydro-3-methoxycarbonylmethyl-2,2,6-trimethyl-1(2H)-naphthalenone

: 119371-64-1
(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

Guidance literature:: In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) RT;
DOI:10.1016/S0040-4020(01)90097-3

Reference yield:

: 14888-09-6,82509-30-6,83846-91-7
ammonium salt of (-)-10-camphorsulfonic acid

: 119371-64-1
(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

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:

: 70591-46-7
(S)-5-methoxycarbonylmethyl-6,6-dimethyl-2-cyclohexen-1-one

: 119371-64-1
(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

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