O-Tetrahydropyranyl Lubiprostone

Base Information

• Chemical Name: O-Tetrahydropyranyl Lubiprostone
• CAS No.: 876068-08-5
• Molecular Formula: C₂₅H₄₀F₂O₆
• Molecular Weight: 474.586
• Mol file: 876068-08-5.mol

Synonyms:

Chemical Property of O-Tetrahydropyranyl Lubiprostone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

O-TetrahydropyranylLubiprostone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected precursor to Lubiprostone.

Technology Process of O-Tetrahydropyranyl Lubiprostone

There total 21 articles about O-Tetrahydropyranyl Lubiprostone 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: 94.0%

C25H42F2O6 → 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (876068-08-5)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; In water; toluene; at 0 ℃; for 0.333333h; pH=6.88; phosphate buffer;

Reference yield: 84.0%

7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (946081-31-8) → 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (876068-08-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 14h;

Reference yield:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (876068-08-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / toluene / 1 h / -75 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -5 °C / Inert atmosphere

2.2: 2 h / 0 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C / 760.05 Torr

5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

6.1: dichloromethane / 6 h / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C

8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

9.1: lithium hydroxide / tert-butyl methyl ether / 1 h / 20 °C / Inert atmosphere

9.2: 36 h / 45 °C

10.1: palladium 10% on activated carbon / water; ethyl acetate / 2 h / 20 °C

11.1: lithium hydroxide / tetrahydrofuran; water; ethanol / 2 h / 20 °C

12.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; tert-butyl methyl ether; water; ethyl acetate; toluene; 6.1: |Wittig Rearrangement / 8.1: |Dess-Martin Oxidation / 12.1: |Dess-Martin Oxidation;

upstream raw materials:

3,4-dihydro-2H-pyran

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Refernces

• 1、 -. "The preparation method of the ruby's forefront". . . Retrieved 2018/04/01.