16(R)-AFP 07 (free acid)

Base Information

• Chemical Name: 16(R)-AFP 07 (free acid)
• CAS No.: 773825-80-2
• Molecular Formula: C₂₂H₃₀F₂O₅
• Molecular Weight: 412.474
• Mol file: 773825-80-2.mol

Synonyms:16(R)-AFP 07 (free acid)

Chemical Property of 16(R)-AFP 07 (free acid)

Chemical Property:

• PSA: 86.99000
• LogP: 3.51300

Purity/Quality:

99% ^*data from raw suppliers

16(R)-AFP 07 (free acid) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 16(R)-AFP 07 (free acid)

There total 8 articles about 16(R)-AFP 07 (free acid) 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:

5-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-non-1-en-6-ynyl]-3,3-difluoro-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid (761425-48-3) → 7,7-difluoro-16S,20-dimethyl-18,19-didehydro prostaglandin I2 (773825-80-2)

Guidance literature:

With acetic acid; In tetrahydrofuran;

DOI:10.2533/000942904777678073

Reference yield:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) → 7,7-difluoro-16S,20-dimethyl-18,19-didehydro prostaglandin I2 (773825-80-2)

Guidance literature:

Multi-step reaction with 8 steps

1: DCC; DMSO

2: NaH / 1,2-dimethoxy-ethane

3: p-TsOH / methanol

4: diisobutylaluminum 2,6-di(tert-butyl)-4-methylphenoxide

5: imidazole / dimethylformamide

6: MnBr₂; KN(SiMe₃)2; (PhSO₂)2NF

7: NaN(SiMe₃)2 / tetrahydrofuran / 0 °C

8: aq. AcOH / tetrahydrofuran

With 1H-imidazole; manganese(II) bromide; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; N-fluorobis(benzenesulfon)imide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1: Moffatt oxidation / 2: Horner-Emmons reaction / 7: Wittig reaction;

DOI:10.2533/000942904777678073

Reference yield:

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde (32233-41-3) → 7,7-difluoro-16S,20-dimethyl-18,19-didehydro prostaglandin I2 (773825-80-2)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / 1,2-dimethoxy-ethane

2: p-TsOH / methanol

3: diisobutylaluminum 2,6-di(tert-butyl)-4-methylphenoxide

4: imidazole / dimethylformamide

5: MnBr₂; KN(SiMe₃)2; (PhSO₂)2NF

6: NaN(SiMe₃)2 / tetrahydrofuran / 0 °C

7: aq. AcOH / tetrahydrofuran

With 1H-imidazole; manganese(II) bromide; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; toluene-4-sulfonic acid; acetic acid; N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1: Horner-Emmons reaction / 6: Wittig reaction;

DOI:10.2533/000942904777678073

upstream raw materials:

5-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-non-1-en-6-ynyl]-3,3-difluoro-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-4-methyl-3-oxo-non-1-en-6-ynyl)-hexahydro-cyclopenta[b]furan-2-one

Refernces