Tetrahydrofuran → 1alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene

HRID 1268498ノート

反応式

HRID 1268498 の反応式
[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].Br[CH2:42][CH2:43][C:44]([CH2:48]C)([OH:47])[CH2:45][CH3:46].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][CH2:48][C:44]([CH2:45][CH3:46])([OH:47])[CH2:43][CH3:42])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 12019512HCID 12019512、化合物HCID 155080001-Bromo-3-ethyl-3-pentanol

生成物 1

HCID 120195171alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene収率 121.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Under the same conditions as in Example 3, 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-phenoxycarbonylthiopregna-5,7,16-triene (82.8 mg, 0.143 mmol), 5-bromo-3-ethyl-3-pentanol (139 mg, 0.715 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 99.6 mg of a product, which was directly used in the subsequent reaction because it was difficult to separate from 5-bromo-3-ethyl-3-pentanol.

後処理

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

出典と根拠

ORDレコード
ord-36293565da714aeeac8fdb29e2195341
出典データセット
uspto-grants-2003_04
特許番号
US06555699B2

反応ノート

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