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

HRID 1268496노트

반응식

HRID 1268496 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(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].Br[CH2:42][CH2:43][CH2:44][CH2:45][C:46]([CH3:49])([OH:48])[CH3:47].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][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([OH:48])([CH3:49])[CH3:47])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 114468866-Bromo-2-methyl-2-hexanolHCID 12019512HCID 12019512, 화합물

생성물 1

HCID 120195151alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(5-hydroxy-5-methyihexylthio)pregna-5,7,16-triene수율 106.8%

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 (82.6 mg, 0.142 mmol), 6-bromo-2-methyl-2-hexanol (139 mg, 0.710 mmol), tetrahydrofuran (1 ml) and 1M KOH solution in methanol (1 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethyl acetate=8:1, developed once) to give 87.2 mg of a product, which was directly used in the subsequent reaction because it was difficult to separate from 6-bromo-2-methyl-2-hexanol.

후처리

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

출처 및 근거

ORD 기록
ord-ebeafed516ab41d78faf77a57cb04c17
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555699B2

반응 노트

불러오는 중…