Reaction #50191

ord-ef9326ee0f3942f8a404fe41d999ff39

Reaction equation

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

Reactants

—
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

Reagents

None

Solvents

ClCCl
methylene chloride

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 (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.v1Patent: US05426115uspto-grants-1995_06