Reaktion #50191

ord-ef9326ee0f3942f8a404fe41d999ff39

Reaktionsgleichung

CCCCCC(/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1O)O[Si](C)(C)C(C)(C)C
(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one
C1=COCCC1
dihydropyran
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesufonate
→
CCCCCC(/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC1CCCCO1)O[Si](C)(C)C(C)(C)C
title compound ( 46 )
CCCCCC(/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC1CCCCO1)O[Si](C)(C)C(C)(C)C
(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

Edukte

—
resultant mixture
CCCCCC(/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1O)O[Si](C)(C)C(C)(C)C
(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one
C1=COCCC1
dihydropyran
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesufonate

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

To a solution of (1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one (45) (4.69 g) in methylene chloride were added dihydropyran (5.17 g), and pyridinium p-toluenesufonate (0.77 g), and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to the silica gel column chromatography to give the title compound (46) as a mixture of the diastereomers.

Quelle

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