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

Base Information

• Chemical Name: 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
• CAS No.: 307928-71-8
• Molecular Formula: C₂₀H₂₈O₅S
• Molecular Weight: 380.505

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 4 articles about 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 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: 89.0%

acetic anhydride (108-24-7) + (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) → 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 (307928-71-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; Ambient temperature;

DOI:10.1039/c39920000341

Reference yield:

3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8) → 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 (307928-71-8)

Guidance literature:

Multi-step reaction with 4 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

4: 89 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

With dmap; 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; pyridine; hexane; dichloromethane;

Reference yield:

3-methyl-2-(prop-2-enyl)-2,5-dihydrothiophene 1,1-dioxide (94987-58-3) → 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 (307928-71-8)

Guidance literature:

Multi-step reaction with 3 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

3: 89 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

With dmap; 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; pyridine; hexane; dichloromethane;

upstream raw materials:

acetic anhydride

(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

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

7β-acetoxy-4,8β,13-trimethyl-19-norpodocarpa-3,12-dien-14-one

C₂₇H₃₄N₂O₄S

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