HRID39613

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14797

Potassium hydroxide

HKO

结构：CCCCC[C@@H](/C=C/[C@@H]1[C@@H](Cc2cccc(OCc3ccccc3)c2)[C@@H](COS(C)(=O)=O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C

HCID86677383

未命名化合物

PRODUCTS

生成物

结构：CCCCC[C@@H](/C=C/[C@@H]1[C@@H](Cc2cccc(O)c2)[C@@H](COS(C)(=O)=O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C

HCID86677382

未命名化合物

收率 127.2%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23938

Palladium

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl methanesulfonate (45 g, 0.06 mol) in dry methanol (450 ml) was treated with potassium hydroxide (9.72 g, 0.18 mol), then with 5% Pd/C (13.5 g, 30% wt) under hydrogen for 2 hr. Then, the reaction mixture was filtered with celite pad. The filtrate was concentrated to obtain crude product (50 g).

WORKUP

后处理

filtrationThen, the reaction mixture was filtered with celite pad
concentrationThe filtrate was concentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-da3a7050e8bd4ead919af4431dbf2100
来源数据集: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08524939B2
来源说明: uspto-grants-2013_09

反应 SMILES

[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:11][C@@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@H:9](/[CH:20]=[CH:21]/[C@@H:22]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:8]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43]CC2C=CC=CC=2)[CH:38]=1)(=[O:4])=[O:3].[OH-].[K+]>CO.[Pd]>[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:11][C@@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[C@H:9](/[CH:20]=[CH:21]/[C@@H:22]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:8]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([OH:43])[CH:38]=1)(=[O:4])=[O:3]