Potassium Hydroxide → 22,29-EPOXY-3,29-DIHYDROXY-14beta-STIGMASTAN-15-ONE

HRID 48958

반응식

HRID 48958 반응식
[O:1]1[CH:6]([OH:7])[CH2:5][C@@H:4]([CH:8]([CH3:10])[CH3:9])[CH2:3][CH:2]1[C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[CH:20]([CH2:21][CH:22]([OH:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[C:15](=[O:33])[CH2:14]1)[CH3:12].[OH-].[K+]>CO>[O:1]1[CH:6]([OH:7])[CH2:5][C@@H:4]([CH:8]([CH3:10])[CH3:9])[CH2:3][CH:2]1[C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[CH:20]([CH2:21][CH:22]([OH:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[C:15](=[O:33])[CH2:14]1)[CH3:12]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 5390213622,29-Epoxy-3,29-dihydroxy-14alpha-stigmastan-15-one

생성물 1

HCID 6962581522,29-EPOXY-3,29-DIHYDROXY-14beta-STIGMASTAN-15-ONE

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Epimerization of compound 248 at the C14 position using KOH in MeOH yields 22,29-epoxy-3,29-dihydroxy-14β-stigmastan-15-one (260). Compound 248 is dissolved in MeOH and a solution of KOH in MeOH (25 mg/ml) is added. The mixture is refluxed for 15 minutes then cooled to room temperature. Water is added and the aqueous slurry is extracted with chloroform and then dried over MgSO4. Filtration and concentration gives the crude product that contains an epimeric mixture of compounds 248 and 260. Separation of 248 and 260 is achieved using column chromatography.

출처 및 근거

ORD 기록
ord-fb8b473e4cc04ca99f6ff93f6ada0203
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706701B1

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