Reaction #50192

ord-3ad8fe52e6fe44e9b186234e310e1315

Reaction equation

CCCCCC(O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
methyl 5(RS)-fluoro-6-oxo-7-{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bis-tetrahydropyranyloxy-cyclopentyl]-6-oxo-heptanoate
CCCCCC(O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
methyl 5(RS)-fluoro-7-{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bistetrahydropyranyloxycyclopentyl]-6-oxoheptanoate
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
CCCCCC(=O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
title compound ( 55 )
CCCCCC(=O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
methyl 5(RS)-fluoro-7-{(1R,2R,3R,5S)-2-[3-oxo-octyl]-3,5-bistetrahydropyranyloxycyclopentyl]-6-oxoheptanoate

Reactants

—
resultant mixture
CCCCCC(O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
methyl 5(RS)-fluoro-6-oxo-7-{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bis-tetrahydropyranyloxy-cyclopentyl]-6-oxo-heptanoate
CCCCCC(O)CC[C@@H]1[C@@H](CC(=O)C(F)CCCC(=O)OC)[C@@H](OC2CCCCO2)C[C@H]1OC1CCCCO1
methyl 5(RS)-fluoro-7-{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bistetrahydropyranyloxycyclopentyl]-6-oxoheptanoate
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONThe reaction mixture was treated in the conventional manner
  2. 2
    Otherthe obtained crude product

Procedure

To a solution of methyl 5(RS)-fluoro-6-oxo-7-{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bis-tetrahydropyranyloxy-cyclopentyl]-6-oxo-heptanoate (54) (0.30 g) in acetone was added Jones reagent (2.60M, 0.6 ml) and the resultant mixture was stirred at -30° C. for 1.5 hours. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to silica gel column chromatography to give the title compound (55) as a mixture of diastereomers.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05426115uspto-grants-1995_06