Glycosidation of Sugars: Ii. Methanolysis of D-Xylose, D-Arabinose, D-Lyxose, and D-Ribose

Bishop, C. T.; Cooper, F. P.

doi:10.1139/v63-405

Cited by 117 publications

(23 citation statements)

References 17 publications

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“…T h a t is, the anomer in which the C-1 methyl group is trans to the C-2 substituent is eluted faster. This observation supports those of Bishop and Cooper (10,13), Ryan et al (16), and Kircher (2).…”

Section: Ry$supporting

confidence: 89%

“…The exceptions were methyl 2,3,5-tri-0-methyl-L-arabinofuranoside, in which the two anomers mere fully separated, and the methyl 2,3-di-O-methyl-4-and -5-0-acetyl-L-arabinosides, which gave not two but three peaks. In the latter case, by using Bishop's quantitative results of glycoside formation (13), and the fact that in no case were the arabinopyranoside anomers separated on this column, the two faster peaks were assigned to the furanoside forms and the slow peak to the pyranosides. All of the acetylated methyl O-methylarabinosides investigated could be distinguished from each other, except for the 5-O-methyl and 3,4-di-O-methyl glycoside derivatives.…”

Section: Ry$mentioning

confidence: 99%

“…The riboside peaks were assigned on the knowledge that under the conditions of glycoside formation the pyranoside forms predominated, and, of these, the 0-anomer was the main form (13).…”

Section: Ry$mentioning

confidence: 99%

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The synthesis, separation, and identification of the methyl ethers of arabinose and their derivatives

Williams¹,

Jones²

1967

Can. J. Chem.

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Section: Ry$supporting

confidence: 89%

Section: Ry$mentioning

confidence: 99%

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The synthesis, separation, and identification of the methyl ethers of arabinose and their derivatives

Williams¹,

Jones²

1967

Can. J. Chem.

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“…15). Compounds ~$ 3 , ~$ 4 , and a,p5 were synthesized as mixtures according to published methods (13). Their identities were checked by comparison of 13C chemical shifts with values published (3).…”

Section: Methodsmentioning

confidence: 99%

A survey of the proton spin–lattice relaxation rates of selected furanose derivatives

Bock¹,

Hall²,

Pedersen³

1980

Can. J. Chem.

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The non-selective proton spin–lattice relaxation rates of 3,5-di-O-acetyl-2,6-dibromo-2,6-dideoxy-D-mannono (1), or -glucono (2), 1,4-lactone, methyl-α,(β)-D-ribofuranoside (3), methyl-α,(β)-D-arabinofuranoside (4), methyl-α(β)-D-xylofuranoside (5), 3,5-di-O-acetyl-1-O-benzoyl-2,6-dibromo-2,6-dideoxy-α and β-D-mannofuranose (6) and (7), 3,5-di-O-acetyl-6-bromo-2,6-dideoxy-D-arabino-1,4-lactone (8), and 2,3,5,6-tetra-O-acetyl-1,4-anhydro-D-mannitol (9) have been measured at 270 MHz. Substantial differences are found for the R1-values of epimeric pairs of substances which can be used for structural evidence. The anomalous R1-values in deuteriochloroform for the H-2, H-3, and H-4 resonances of 1 are discussed.

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“…The previous paper (1) in this series described a study of the lcinetics of metl~anolysis of the four D-pentoses. As a prelude to extending this work to the hexoses it was necessary to find methods for analyzing the methyl hexosides by gas-liquid chromatography.…”

mentioning

confidence: 99%

GLYCOSIDATION OF SUGARS: II. GAS–LIQUID CHROMATOGRAPHY OF THE METHYL GLYCOSIDES OF D-GALACTOSE, D-GLUCOSE, AND D-MANNOSE AS THEIR TRIMETHYLSILYL ETHERS

Smirnyagin¹,

Bishop²,

Cooper³

1965

Can. J. Chem.

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The previous paper (1) in this series described a study of the lcinetics of metl~anolysis of the four D-pentoses. As a prelude to extending this work to the hexoses it was necessary to find methods for analyzing the methyl hexosides by gas-liquid chromatography. The present communication describes the gas-liquid chromatographic separation of the four methyl glycosides of each of the three aldohexoses, D-galactose, D-glucose, and D-mannose.Unsubstituted methyl glycosides are considerably less volatile than Inany other derivatives in which some of the hydroxyl groups of the sugar ring are substituted bj, ester or ether groups. Nevertheless, gas-liquid chromatography of a number of unsubstituted methyl glycosides has been described (2, 3). However, the conditions required for these separations vrere not sufficiently selective to resolve the four isomeric glycosides of a single monosaccharide. In the previous studies in this series (1, 4) the methyl glycosides were 0-inethylated or 0-acetylated to make them sufficiently volatile for analysis by gas-liquid chromatography. In the present study it was found that the 0-trimethylsilyl derivatives of the methyl hexosides could be resolved better than either the 0-acetyl or the 0-methyl derivatives. The use of 0-trimethylsilyl derivatives has the advantage of ease of preparation and simple recovery of the original con~pound by a very mild hydrolysis ( 5 ) . The separations described here may therefore also be used on a preparative scale to provide pure sainples of individual methyl glycosides for spectroscopic examination or studies of kinetics of hydrolysis.The retention times of the methyl tetra-0-trimethylsilyl hexosides and of the trimethylsilyl tetra-0-triinethylsilyl hexosides, relative to the fastest moving componeilt in each series, are shown in Table I. Three column pacltings nrere used and each required a different column temperature for optiinuin resolution. The crystalline hexoses each gave only one peak after trimethylsilylation; it is not kno\vn whether these single pealts contained more than one anomer or ring form. However, it is likely that the hexoses underwent trimethylsilylation before equilibration in the pyridine solution. If this was so, then the single pealts for each hexose must represent the anomeric species present in the common crystalline forin of the sugar. This is in agreement with the results of S\\.eeley et al. (6), who found that "the products obtained from pure single anomers of pentoses and hexoses generally show a single peak on gas chromatography though, in some cases, small amounts of another anonleric form may be apparent. In general, anoinerizations occurring in pyridine during preparation of the trimethylsilyl derivative are remarkably minimal."The four methyl D-mannosides were well resolved on columns a or b, with the latter providing slightly better separation. Similarly, the four methyl D-glucosides were resolved on columns b or c but the separation was significantly improved on the latter column. The four methyl D-galactosides ...

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Glycosidation of Sugars: Ii. Methanolysis of D-Xylose, D-Arabinose, D-Lyxose, and D-Ribose

Cited by 117 publications

References 17 publications

The synthesis, separation, and identification of the methyl ethers of arabinose and their derivatives

The synthesis, separation, and identification of the methyl ethers of arabinose and their derivatives

A survey of the proton spin–lattice relaxation rates of selected furanose derivatives

GLYCOSIDATION OF SUGARS: II. GAS–LIQUID CHROMATOGRAPHY OF THE METHYL GLYCOSIDES OF D-GALACTOSE, D-GLUCOSE, AND D-MANNOSE AS THEIR TRIMETHYLSILYL ETHERS

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