Accession Number:

AD0442461

Title:

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

Descriptive Note:

Corporate Author:

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

Personal Author(s):

Report Date:

1963-12-20

Pagination or Media Count:

8.0

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

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Distribution Statement:

APPROVED FOR PUBLIC RELEASE