Réaction #50191

ord-ef9326ee0f3942f8a404fe41d999ff39

Équation de réaction

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

Réactifs

—
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

Réactifs

Aucun

Solvants

ClCCl
methylene chloride

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05426115uspto-grants-1995_06