Synthesis and mass spectra of 4-O-acetyl-1,5-anhydro-2,3,6-tri-O -(methoxycarbonylmethyl)-D-glucitol and the positional isomers of 4- O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methyl-D-glucitol and 4-O-acetyl-1,5-anhydro-O-(methoxycarbonylmethyl)-di-O-methyl-D-glucitol .
Reductive cleavage of fully methylated, partially O-carboxymethylated cellulose had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -2-O-(methoxycarbonylmethyl)-3,6-di-O-methyl-, -3-O-(methoxycarbonylmethyl)-2,6-di-O-methyl-, -6-O-(methoxycarbonylmethyl)-2,3-di-O-methyl-, -2,3-di-O-(methoxycarbonylmethyl)-6-O-methyl-, -2,6-di-O-(methoxycarbonylmethyl)-3-O-methyl-, -3,6-di-O-(methoxycarbonylmethyl)-2-O-methyl-, and -2,3,6-tri-O-(methoxycarbonylmethyl)-D-glucitol. Described herein is the independent synthesis of these derivatives, except for the first, which had been reported. In addition, their 1H-n.m.r. spectra, chemical-ionization (NH3) mass spectra, and electronionization mass spectra are tabulated.
Zeller
S G
SG
Department of Chemistry, University of Minnesota, Minneapolis 55455.
Griesgraber
G W
GW
Gray
G R
GR
D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry; D015394:Molecular Structure; D011522:Protons; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000737:chemistry
D011522:Protons; C072432:4-O-acetyl-1,5-anhydro-O-(methoxycarbonylmethyl)di-O-methylglucitol; C072431:4-O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methylglucitol; C072430:4-O-acetyl-1,5-anhydro-2,3,6-tri-O-(methoxycarbonylmethyl)glucitol; D013012:Sorbitol