Tetrahydrofuran → 1alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(2-hydroxy-2-methylpropylthio)pregna-5,7,16-triene

HRID 1268497노트

반응식

HRID 1268497 반응식
[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][C:24](OC2C=CC=CC=2)=O)[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:41][C:42]1([O:45]C1)[CH3:43].O1CCCC1.[OH-].[K+]>CO>[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][C:42]([OH:45])([CH3:43])[CH3:41])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11208Isobutylene oxideHCID 14797Potassium HydroxideHCID 12019512HCID 12019512, 화합물

생성물 1

HCID 120195161alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(2-hydroxy-2-methylpropylthio)pregna-5,7,16-triene수율 82%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Under the same conditions as in Example 3, 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-phenoxycarbonylthiopregna-5,7,16-triene (83.0 mg, 0.143 mmol), isobutylene oxide (113 mg, 1.56 mmol), tetrahydrofuran (0.5 ml) and 1M KOH solution in methanol (0.5 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane:ethyl acetate=1:1, developed once) to give the title compound as a colorless oil (62.3 mg, 82%).

후처리

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane

출처 및 근거

ORD 기록
ord-51baa25390fd4afb8718f0ce468b7f73
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555699B2

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