3,4-dihydro-2H-pyran → (1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyl-dimethylsilyloxy-1-octenyl]-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

HRID 486166Notes

Reaction equation

HRID 486166 reaction equation
[Si:1]([O:8][CH:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:10]=[CH:11]/[C@H:12]1[C@H:19]([OH:20])[CH2:18][C@H:17]2[C@@H:13]1[CH2:14][C:15](=[O:21])[O:16]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:10]=[CH:11]/[C@H:12]1[C@H:19]([O:20][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[CH2:18][C@H:17]2[C@@H:13]1[CH2:14][C:15](=[O:21])[O:16]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15224603(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one

Product 1

HCID 15224604(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyl-dimethylsilyloxy-1-octenyl]-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude product

Sources & evidence

ORD record
ord-2da28dd4c0f3434e9e933eeefe613b73
Source dataset
uspto-grants-1994_03
Patent number
US05290811

Reaction notes

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