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 21913노트

반응식

HRID 21913 반응식
[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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ef9326ee0f3942f8a404fe41d999ff39
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426115

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