Synthesis and mass spectra of 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-ethyl-D-glucitol and the positional isomers of 4-O-acetyl-1,5-anhydro-di-O-ethyl-O- methyl-D-glucitol and 4-O-acetyl-1,5-anhydro-O-ethyl-di-O-methyl-D-glucitol.
Reductive cleavage of fully methylated, partially O-ethylated cellulose or fully ethylated, partially O-methylated cellulose and subsequent acetylation had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -6- O-ethyl-2,3-di-O-methyl-, -3-O-ethyl-2,6-di-O-methyl-, -2-O-ethyl-3,6-di-O- methyl-, -2,3-di-O-ethyl-6-O-methyl-, -2,6-di-O-ethyl-3-O-methyl-, -3,6-di-O- ethyl-2-O-methyl-, and -2,3,6-tri-O-ethyl-D-glucitol. Described herein is the independent synthesis of these derivatives, except for the first (which had been reported); and their 1H-n.m.r. spectra, chemical-ionization (NH3) mass spectra, and electron-impact mass spectra are tabulated.
Zeller
S G
SG
Department of Chemistry, University of Minnesota, Minneapolis 55455.
D'Ambra
A J
AJ
Rice
M J
MJ
Gray
G R
GR
D055598:Chemical Phenomena; D002621:Chemistry; D005019:Ethyl Ethers / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008738:Methyl Ethers / Q000032:analysis / Q000138:chemical synthesis; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D013237:Stereoisomerism
D005019:Ethyl Ethers; D008738:Methyl Ethers; C059249:4-O-acetyl-1,5-anhydro-2,3,6-tri-O-ethylglucitol; D013012:Sorbitol