(5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone

Base Information

• Chemical Name: (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone
• CAS No.: 307928-72-9
• Molecular Formula: C₁₈H₂₆O₄S
• Molecular Weight: 338.468

Synonyms:(5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone

Chemical Property of (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone

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Technology Process of (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone

There total 3 articles about (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone 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: 87.0%

6-methyl-carvone (158930-44-0) + (3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)acetaldehyde (141257-32-1) → (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone (307928-72-9)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃;

Reference yield:

3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8) → (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone (307928-72-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / NaN2 / tetrahydrofuran / -105 °C

2: 1.) OsO₄, 4-methylmorpholine N-oxide, 2.) NaIO₄ / 1.) 1,4-dioxane, H₂O, room temperature, 24 h, 2.) MeOH, H₂O, room temperature, overnight

3: 87 percent / LDA, DMPU / tetrahydrofuran; hexane / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; osmium(VIII) oxide; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane;

Reference yield:

3-methyl-2-(prop-2-enyl)-2,5-dihydrothiophene 1,1-dioxide (94987-58-3) → (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone (307928-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) OsO₄, 4-methylmorpholine N-oxide, 2.) NaIO₄ / 1.) 1,4-dioxane, H₂O, room temperature, 24 h, 2.) MeOH, H₂O, room temperature, overnight

2: 87 percent / LDA, DMPU / tetrahydrofuran; hexane / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane;

upstream raw materials:

6-methyl-carvone

(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)acetaldehyde

3-methyl-2,5-dihydrothiophen-1,1-dioxide

3-methyl-2-(prop-2-enyl)-2,5-dihydrothiophene 1,1-dioxide

Downstream raw materials:

Acetic acid (E)-(S)-1-((1S,6R)-6-isopropenyl-1,3-dimethyl-2-oxo-cyclohex-3-enyl)-4-methyl-hexa-3,5-dienyl ester

C₂₇H₃₄N₂O₄S

Acetic acid (S)-1-((1S,6R)-6-isopropenyl-1,3-dimethyl-2-oxo-cyclohex-3-enyl)-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl ester

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