methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate

Base Information

• Chemical Name: methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate
• CAS No.: 267899-13-8
• Molecular Formula: C₁₉H₂₂O₅S
• Molecular Weight: 362.447

Synonyms:methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate

Chemical Property of methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate

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Technology Process of methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate

There total 4 articles about methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D^3(3aH),α-acetate 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: 38.0%

methyl 4-hydroxy-2-butynoate (31555-05-2) + 4,4-dimethyl-2-[(S)-p-tolylsulfinyl]-2-cyclopenten-1-one (267899-12-7) → methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D3(3aH),α-acetate (267899-13-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/ja994053w

Reference yield:

2-bromo-4,4-dimethylcyclopent-2-en-1-one (21428-66-0) → methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D3(3aH),α-acetate (267899-13-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / camphorsulfonic acid / benzene / Heating

2.1: n-butyllithium / tetrahydrofuran; hexane

2.2: 77 percent / tetrahydrofuran; hexane

3.1: camphorsulfonic acid; water / acetone / 15 h / 20 °C

4.1: 38 percent / K₂CO₃ / tetrahydrofuran / 5 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; water; potassium carbonate; In tetrahydrofuran; hexane; acetone; benzene; 1.1: ketalization / 2.1: Metallation / 2.2: Tosylation / 3.1: deketalization / 4.1: tandem Michael reaction;

DOI:10.1021/ja994053w

Reference yield:

6-bromo-8,8-dimethyl1,4-dioxaspiro<4.4>non-6-ene (120584-77-2) → methyl (3aS,6aR)-4,5,6,6a-tetrahydro-6,6-dimethyl-4-oxo-3a-[(S)-p-tolylsulfinyl]-2H-cyclopenta[b]furan-D3(3aH),α-acetate (267899-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane

1.2: 77 percent / tetrahydrofuran; hexane

2.1: camphorsulfonic acid; water / acetone / 15 h / 20 °C

3.1: 38 percent / K₂CO₃ / tetrahydrofuran / 5 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; water; potassium carbonate; In tetrahydrofuran; hexane; acetone; 1.1: Metallation / 1.2: Tosylation / 2.1: deketalization / 3.1: tandem Michael reaction;

DOI:10.1021/ja994053w

upstream raw materials:

methyl 4-hydroxy-2-butynoate

4,4-dimethyl-2-[(S)-p-tolylsulfinyl]-2-cyclopenten-1-one

2-bromo-4,4-dimethylcyclopent-2-en-1-one

6-bromo-8,8-dimethyl1,4-dioxaspiro<4.4>non-6-ene

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