Chemical Synthesis and Structure Proof of a Stereoregular Linear Mannan, Poly-α-(1→6′)-anhydro-D-mannopyranose

Jean Frechet, Conrad Schuerch

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62 Scopus citations

Abstract

Stereoregular poly-α-(1→6′)-anhydro-D-mannopyranose has been synthesized by the phosphorus pentafluoride initiated polymerization of 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-mannopyranose at –78˚ in methylene chloride, followed by debenzylation of the polymeric derivative with sodium in liquid ammonia. The polymer, isolated as a hemihydrate, [α]30D 121.5-122.8˚ (1 % in DMSO), forms cloudy solutions in water and clear solutions in dimethyl sulfoxide. On periodate oxidation, this polymer consumes the theoretical amount of oxidant and produces the theoretical amount of formic acid. After oxidation the optical rotation of both the synthetic mannan and a synthetic stereoregular poly-α-(1rarr;6′)-anhydro-D-glucopyranose are identical. Less stereoregular mannas have been synthesized from the corresponding triacetate and after oxidation show lower positive rotations.

Original languageEnglish (US)
Pages (from-to)1161-1164
Number of pages4
JournalJournal of the American Chemical Society
Volume91
Issue number5
DOIs
StatePublished - Jan 1 1969

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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