HRID1974778

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7397

p-Toluenesulfonyl chloride

C7H7ClO2S

结构：C=C1C[C@@H]2[C@H](/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2C1O

HCID13955240

未命名化合物

PRODUCTS

生成物

结构：C=C1C[C@@H]2[C@H](/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2C1OS(=O)(=O)c1ccc(C)cc1

HCID22850343

未命名化合物

收率 78%

PROCEDURE

实验过程

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

后处理

customcolumn-chromatographed

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-67abc28dfaf0416dba3f6cc11f28e860
来源数据集: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05283349
来源说明: uspto-grants-1994_02

反应 SMILES

[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