4-Toluenesulfonyl chloride → (1S,2RS,5S,6S,7R)-2-p-toluenesulfonyloxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

HRID 1974778Notes

Reaction equation

HRID 1974778 reaction equation
[OH:1][CH:2]1[C:9](=[CH2:10])[CH2:8][C@H:7]2[C@@H:3]1[CH2:4][C@@H:5]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@H:6]2/[CH:11]=[CH:12]/[C@@H:13]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>>[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([O:1][CH:2]2[C:9](=[CH2:10])[CH2:8][C@H:7]3[C@@H:3]2[CH2:4][C@@H:5]([O:27][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:29])[CH3:30])[C@H:6]3/[CH:11]=[CH:12]/[C@@H:13]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:43])=[O:42])=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13955240(1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

Product 1

HCID 22850343(1S,2RS,5S,6S,7R)-2-p-toluenesulfonyloxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octaneYield 78%

Procedure

In the same way as in Example 8, (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy- 1-octenyl]-7-t-butyldinmethylsilyloxybicyclo[3.3.0]octane (178 mg, 0.35 mmole) obtained in Example 3 was reacted with p-toluenesulfonyl chloride (133 mg, 0.70 mmole). The reaction mixture was worked up and column-chromatographed to give (1S,2RS,5S,6S,7R)-2-p-toluenesulfonyloxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (179 mg, 0.27 mmole, 78%).

Workup

  1. customcolumn-chromatographed

Sources & evidence

ORD record
ord-67abc28dfaf0416dba3f6cc11f28e860
Source dataset
uspto-grants-1994_02
Patent number
US05283349

Reaction notes

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