By the same authors

From the same journal

DISPLACEMENT-REACTIONS ON 2,3,4,6-TETRA-O-BENZYL-1,5-DI-O-SULFONYL-D-GLUCITOLS - SYNTHESIS OF (3R,4S)-3,4-DIBENZYLOXY-2-(2-BENZYLOXYETHYLIDENE)TETRAHYDROFURAN

Research output: Contribution to journalArticle

Author(s)

  • P A FOWLER
  • A H HAINES
  • R J K TAYLOR
  • E J T CHRYSTAL
  • M B GRAVESTOCK

Department/unit(s)

Publication details

JournalJournal of the Chemical Society-Perkin Transactions 1
DatePublished - 7 May 1993
Issue number9
Number of pages3
Pages (from-to)1003-1005
Original languageEnglish

Abstract

Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-O-benzyl-L-iditol. In contrast, the corresponding 1,5-ditriflate on similar treatment undergoes displacement at C-1 by attack of O-4 and elimination of triflic acid between C-4 and C-5 to afford (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran.

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