Inge M.E. Thiel

Proton and C-13 nuclear magnetic resonance spectra of some benzoylated aldohexoses

Abstract Chemical shifts and coupling constants of 1 H-n.m.r. spectra of the perbenzoates of α- d -glucopyranose ( 1 ), β- d -glucopyranose ( 2 ), α- d -galactopyranose ( 3 ), α- d -mannopyranose ( 4 ), β- d -mannopyranose ( 5 ), and α- d -galactofuranose ( 6 ) are reported. The 13 C-n.m.r. chemical shifts of compounds 1-3 and 6 , and of penta- O -benzoyl-β- d -galactofuranose ( 7 ) are given. Mass spectra were used to differentiate the furanoses 6 and 7 from the pyranose 3 .

Preparation and structure of 1,2,6,2′,3′,4′,6′-hepta-O-benzoyl-β-lactose and 6-O-benzoyllactose

Abstract 1,2,6,2′,3′,4′,6′-Hepta- O -benzoyl-β-lactose ( 1 ) was prepared and its structure ascertained. Ammonolysis gave 6- O -benzoyllactose and lactose. The stability of the 6- O -benzoyl group was investigated and is discussed.

Conformations of some per-O-acetylaldononitriles and 5-(polyacetoxyalkyl)tetrazoles

The conformations of several per-O-acetylaldononitriles and 5-(polyacetoxyalkyl)tetrazoles in pyridine-d5 solution have been studied by p.m.r. spectroscopy. For compounds of both types, those having the arabino, galacto, and manno configurations take an extended, planar, zigzag arrangement for the carbon chain, whereas, for those having the xylo, ribo, and gluco configurations, the values of the coupling constants indicate that a bent conformation is favored.

Synthesis and mass spectra of some 2-methyl and 2-phenyl-5-(polyacetoxyalkyl)-1,3,4-oxadiazoles and their conformations in solution

Abstract The synthesis and mass spectra of some 2-methyl- and 2-phenyl-5-(polyacetoxyalkyl)-1,3,4-oxadiazoles (4-9) are described. The preferred conformations of 4-9 in solution have been determined by p.m.r. spectroscopy.

Preparation and structure of 1,2,6,2,′3′,4′,6′-hepta-O-benzoyl-β-cellobiose and 6-O-benzoylcellobiose

Abstract 1,2,6,2′,3′,4′,6′-hepta- O -benzoyl-β-cellobiose ( 1 ) was prepared and its structure ascertained. Ammonolysis of 1 gave 6- O -benzoylcellobiose and cellobiose.

The reaction of ammonia with acylated disaccharides : Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose

Abstract From the reaction of octa-O-benzoyl-lactose (1) with methanolic ammonia, lactose, 1,1-bis(benzamido)-1-deoxy-4-O-β- D -galactopyranosyl- D -glucitol (2), and N-benzoyl-4-O-β- D -galactopyranosyl- D -glucopyranosylamine (3) were obtained. The behavior of some other octabenzoylated disaccharides in the ammonolysis reaction is discussed.

Synthesis and spectra of some octa-O-benzoylaldo-biononitriles

Abstract 2,3,5,6,2′,3′,4′,6′-Octa- O -benzoyl-cellobiononitrile, -lactobiononitrile, -maltobiononitrile, and 2,3,4,5,2′,3′,4′,6′-octa- O -benzoyl-melibiononitrile were prepared by benzoylation and dehydration of the corresponding disaccharide oximes, and their 1 H- and 13 C-n.m.r., and e.i.m.s. spectra are described.

Mass spectra of some per-O-benzoylated aldopyranoses and aldofuranoses

Abstract Mass spectra by electron impact-ionization of penta- O -benzoyl derivatives of α- d -glucopyranose, β- d -glucopyranose, α- d -glucofuranose, α- d -galactopyranose, α- d -galactofuranose, β- d -galactofuranose, α- d -mannopyranose, and β- d -mannopyranose, and of tetra- O -benzoyl derivatives of α- d -xylopyranose, α- d -lyxopyranose, β- d -ribopyranose, and β- l -arabinopyranose are reported. Their fragmentation pattern is proposed and the fragments useful for diagnostic purposes are presented.

13C-N.M.R. spectra of some acyclic perbenzoylated carbohydrate derivatives

Abstract The 13 C-n.m.r. spectra of twelve perbenzoylated alditols, ten perbenzoylated aldononitriles, six 5-(polybenzoyloxyalkyl)tetrazoles, and six 5-(polyhydroxyalkyl)tetrazoles are described and their correlations are discussed.

Mass spectra of some benzoylated, acyclic-monosaccharide derivatives

Abstract Mass spectra of some benzoylated aldononitriles and 5-[poly(benzoyloxy)alkyl] tetrazoles are described, and their fragmentation patterns proposed.