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-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.
D000107:Acetylation; D000478:Alkylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008351:Mannans; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013058:Mass Spectrometry; D008745:Methylation; D012441:Saccharomyces cerevisiae / Q000032:analysis*
D007202:Indicators and Reagents; D008351:Mannans; D008353:Mannitol; C042618:1,5-anhydro-mannitol