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

HRID 1268496ノート

反応式

HRID 1268496 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(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]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 114468866-Bromo-2-methyl-2-hexanolHCID 12019512HCID 12019512、化合物

生成物 1

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

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 (82.6 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.

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-ebeafed516ab41d78faf77a57cb04c17
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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