Synthesis and mass spectra of the partially methylated and partially ethylated anhydro-D-mannitol acetates derived by reductive cleavage of permethylated and perethylated Saccharomyces cerevisiae D-mannans

Reductive cleavage of per-O-ethylated or per-O-methylated Saccharomyces cerevisiae D-mannans and subsequent acetylation had previously been shown to produce the expected derivatives of 1,5-anhydro-D-mannitol. Described herein is the independent synthesis of each of these derivatives, namely, 1,5-anh...

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Bibliographic Details
Published in:Carbohydrate research 1984-07, Vol.129, p.87-97
Main Authors: Bowie, J.U, Gray, G.R
Format: Article
Language:English
Subjects:
Acetylation
Alkylation
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mannans
Mannitol - analogs & derivatives
Mannitol - chemical synthesis
Mass Spectrometry
Methylation
Organic chemistry
Preparations and properties
Saccharomyces cerevisiae - analysis
yeasts
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Summary:Reductive cleavage of per-O-ethylated or per-O-methylated Saccharomyces cerevisiae D-mannans and subsequent acetylation had previously been shown to produce the expected derivatives of 1,5-anhydro-D-mannitol. Described herein is the independent synthesis of each of these derivatives, namely, 1,5-anhydro-2,3,4,6-tetra-O-methyl-, -2,3,4,6-tetra-O-ethyl-, -2-O-acetyl-3,4,6-tri-O-methyl-, -2-O-acetyl-3,4,6-tri-O-ethyl-, -3-O-acetyl-2,4,6-tri-O-methyl-, -3-O-acetyl-2,4,6-tri-O-ethyl-, -6-O-acetyl-2,3,4-tri-O-methyl-, -6-O-acetyl-2,3,4-tri-O-ethyl-, -2,6-di-O-acetyl-3,4-di-O-methyl-, -2,6-di-O-acetyl-3,4-di-O-ethyl-, -3,6-di-O-acetyl-2,4-di-O-methyl-, and -3,6-di-O-acetyl-2,4-di-O-ethyl-D-mannitol. The 1H-n.m.r. spectra, chemical-ionization (NH3) mass spectra, and electron-impact mass spectra for all of these derivatives are tabulated.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(84)85301-X