Regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

Kelebekli L., Aksu K., ŞAHİN E.

TETRAHEDRON LETTERS, cilt.59, sa.13, ss.1258-1260, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 13
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.tetlet.2018.02.050
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1258-1260
  • Anahtar Kelimeler: chiro-Inositol, Methoxy conduritol-B, Methoxy inositol, Regio- and stereospecific synthesis, D-CHIRO-INOSITOL, MYOINOSITOL, INHIBITORS
  • Atatürk Üniversitesi Adresli: Evet

Özet

The regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compound, which was reacted with sodium methoxide to produce dimethoxy conduritol-B. Regiospecific bromination of the alkene moiety furnished the desired chiro-inositol derivative. (C) 2018 Published by Elsevier Ltd.