Syntheses of 6-Hydroxycortisol 6-Hemisuccinate

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  • 6-Hydroxycortisol 6-Hemisuccinateの合成
  • 6 Hydroxycortisol 6 Hemisuccinate ノ ゴウセ

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Abstract

The selective acetylation of 17α, 20, 20, 21-BMD-pregnan-5α, 6β, 11β-triol-3-one (IV), derived from cortisone, was led to its 6β-acetate (V). A solution of V in CHCl3 containing EtOH (0.7%) was treated with HCI gas to give 17α, 20, 20, 21-BMD-4-pregnene-6α, 11β-diol-3-one-6-acetate (VIa) and in pure CHCl3 to give 6β-derivative (VIb). The hydrolysis of 6-O-acetate of VIa with K2CO3 followed by succinylation with succinic anhydride gave 17α, 20, 20, 21-BMD-4-pregnene-6α, 11β-diol-3-one 6-hemisuccinate (VIIIa). 6α-Hydroxy- cortisol 6-hemisuccinate (IXa) was obtained by the hydrolysis of the bismethylenedioxy protecting group in VIIIa with 50% AcOH. 6β-Hydroxycortisol 6-hemisuccinate (IXb) was also obtained from VIb by the same procedure.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 95 (2), 185-189, 1975

    The Pharmaceutical Society of Japan

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