Accession Number : AD0442461


Title :   D-MANNOFURANOSE 2,3-CARBONATE. PREFERRED SIZE OF THE SUGAR RING IN SOME FUSED-RING DERIVATIVES,


Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB


Personal Author(s) : Perlin,A S


Report Date : 20 Dec 1963


Pagination or Media Count : 8


Abstract : Treatment of 6-0-trityl-D-mannose with phosgene gives 6-0-trityl-D-mannose 2,3-carbonate (II), which on partial hydrolysis, yields D-mannose 2,3-carbonate (VI). Chemical properties of II and VI agree with the proposition that fusion of the cyclic carbonate group at the 2- and 3-positions of D-mannose converts the latter to a furanose derivative. Nuclear magnetic resonance spectral evidence supports the furanoid assignment and indicates also that in aqueous solution VI does not rearrange significantly o a pyranose form. Substantial disagreement is found between proton-proton coupling observed for VI and corresponding data predicted from the Karplus curve. A similar situation is encountered with a related fused-ring derivative, 2,3-0-isopropylidene-Lrhamnose. (Author)


Descriptors :   HEXOSES , TITRATION , OXYGEN HETEROCYCLIC COMPOUNDS , CANADA , CARBOHYDRATES


Distribution Statement : APPROVED FOR PUBLIC RELEASE