(S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

Base Information

• Chemical Name: (S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol
• CAS No.: 87417-22-9
• Molecular Formula: C₂₈H₄₄O₃S
• Molecular Weight: 460.722

Synonyms:

Chemical Property of (S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

Chemical Property:

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Useful:

Technology Process of (S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol

There total 2 articles about (S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 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:

ergocalciferol (50-14-6,51744-66-2,61177-68-2,116559-84-3,137174-35-7) → (S)-3-[(1R,3aS)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (87407-73-6,87417-22-9,87680-65-7)

Guidance literature:

With sulfur dioxide; In water; benzene;

DOI:10.1021/jo00359a061

Reference yield:

vitamin D2 (50-14-6,51744-66-2,61177-68-2,116559-84-3,137174-35-7) → (S)-3-[(R)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (87407-73-6,87417-22-9,87680-65-7)

Guidance literature:

With sulfur dioxide; for 0.5h; Heating;

DOI:10.1248/cpb.40.1662

Reference yield:

(S)-3-[(1R,3aS)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (87407-73-6,87417-22-9,87680-65-7) → 1α-hydroxyergocalciferol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / ethanol / Heating

2: imidazole / dimethylformamide

3: SeO₂, N-methylmorpholine N-oxide / methanol; CH₂Cl₂ / Heating

4: acridine / Irradiation

5: (C₄H₉)4N¹⁺*F^1- / tetrahydrofuran

With 1H-imidazole; acridine; selenium(IV) oxide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00359a061

upstream raw materials:

ergocalciferol

vitamin D₂

Downstream raw materials:

(S)-4-Methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol

1α-hydroxyergocalciferol

tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexyloxy}-silane

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-3-[2-[(R)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

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