HRID1744792

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3[C@H](CC=Cc4cc(OCc5ccccc5)cc(OCc5ccccc5)c4)C[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

HCID69627056

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3[C@H](CCCc4cc(O)cc(O)c4)C[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

HCID69626928

未命名化合物

收率 43%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23938

Palladium

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

The resulting 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3,5-dibenzyloxyphenyl)-2-propenyl)-5α-androstan-3-one was dissolved in ethyl acetate (3 ml) and stirred in the presence of 10% palladium/carbon (50 mg) at 25° C. for 4 days under hydrogen atmosphere. After the reaction mixture was filtered and evaporated under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3,5-dihydroxyphenyl)propyl)-5α-androstan-3-one (107.5 mg, yield 43%).

WORKUP

后处理

filtrationAfter the reaction mixture was filtered
customevaporated under reduced pressure
customto remove the solvent
customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-af589ffb4fb1432a8fc277d7143b8be5
来源数据集: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07018993B2
来源说明: uspto-grants-2006_03

反应 SMILES

[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH:30]=[CH:31][C:32]1[CH:37]=[C:36]([O:38]CC2C=CC=CC=2)[CH:35]=[C:34]([O:46]CC2C=CC=CC=2)[CH:33]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[C:34]([OH:46])[CH:35]=[C:36]([OH:38])[CH:37]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]