Synthesis of Deuterium-labelled Estriol, 16α-Hydroxyestrone and Estriol 16-Glucuronide via 2,4,16α-Tribromoestrone as Internal Standards for Mass Fragmentography

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概要

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• Synthesis of 1,3,5 (10)-estratriene-3,16α, 17β-triol-d_6 and -d_7 (4), 3,16α-dihydroxy-1,3,5 (10)-estratrien-17-one-d_5 (5) and sodium 3,17β-dihydroxy-1,3,5 (10)-estratrien-16α-yl-β-D-glucopyranosuronate-d_6 (8) is described. Treatment of 2,4,16α-tribromo-3-hydroxy-1,3,5 (10)-estratrien-17-one (1) with sodium hydroxide-OD in deuterium oxide-pyridine under controlled conditions gave the [16β-^2H] 16α-hydroxy-17-one (2). The ketol 2 was converted into the triol-d_6 (4) via sodium borodeuteride reduction in the presence of palladium chloride. Similar treatment of the 17-ethyleneacetal of 2 followed by acid hydrolysis gave compound 5-d_5. Reaction of 2 with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranosuronate using silver carbonate as a catalyst yielded the 16-monoglucuronide acetate methyl ester (6). The reductive removal of the bromines of 6 and subsequent alkaline hydrolysis gave the glucuronide-d_6 (8). Mass spectrometric analysis showed compounds 4,5,and 8 to have good isotopic purity.

• 公益社団法人日本薬学会の論文
• 1984-02-25

著者

• 沼沢 光輝

  Tohoku Pharmaceutical University

• 沼沢 光輝

  Tohoku College Of Pharmacy

• 長岡 正男

  東北薬科大学

• 長岡 正男

  Tohoku College of Pharmacy

• 尾形 美恵子

  Tohoku College of Pharmacy

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