ABSTRACT
Described herein is the synthesis of eight positional isomers of methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside. The compounds were generated simultaneously from methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside by sequential partial methylation and benzoylation and isolated in pure form by high-performance liquid chromatography (HPLC). The desired acetates were obtained by debenzoylation and acetylation of the pure isomers. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative. Also reported for the acetates and the tri-O-methyl derivative are their linear temperature-programmed gas-liquid chromatography (GLC) retention indices on three different capillary columns.
Subject(s)
Acetates/chemistry , Acetylglucosamine/analogs & derivatives , Glucosides/chemical synthesis , Acetylation , Acetylglucosamine/chemical synthesis , Acetylglucosamine/chemistry , Benzoates/chemistry , Chromatography, Gas , Chromatography, High Pressure Liquid , Glucosides/chemistry , Isomerism , Magnetic Resonance Spectroscopy , Mass Spectrometry/methods , Methylation , Molecular Structure , Reference StandardsABSTRACT
Described herein is the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-L-arabinitol. The compounds were generated simultaneously from 1,5-anhydro-L-arabinitol by sequential partial methylation and benzoylation and isolated in pure from by high-performance liquid chromatography. The desired acetates were obtained by debenzoylation and acetylation of the pure isomers. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative. Also reported for the acetates and the tri-O-methyl derivative are their linear temperature-programmed gas-liquid chromatography retention indices on three different capillary columns.
Subject(s)
Sugar Alcohols/chemistry , Acetylation , Benzoates/analysis , Carbohydrate Conformation , Chromatography, Gas , Chromatography, Liquid , Isomerism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Methylation , Reference Standards , Sugar Alcohols/isolation & purificationABSTRACT
Described herein is the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-L-fucitol. The benzoates are generated simultaneously from 1,4-anhydro-L-fucitol by sequential partial methylation and benzoylation or sequential partial benzoylation and methylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation provided the corresponding acetates. The 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative are reported herein as are the linear temperature programmed gas-liquid chromatography retention indices of the acetates and the tri-O-methyl derivative on three different capillary columns.
Subject(s)
Sugar Alcohols/chemistry , Acetates/chemical synthesis , Acetates/chemistry , Acetylation , Benzoates/chemical synthesis , Benzoates/chemistry , Chromatography, Gas , Isomerism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Methylation , Molecular Structure , Oxidation-Reduction , Reference Standards , Sugar Alcohols/chemical synthesis , Sugar Alcohols/standardsABSTRACT
Described herein is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-mannitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-mannitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation of the latter and acetylation yielded the desired acetates. The the benzoates and the electron-ionization mass spectra of the acetates and the tetra-O-methyl derivative are reported herein as are the linear temperature-programmed gas-liquid chromatography retention indices of the acetates and the tetra-O-methyl derivative on three different capillary columns.
Subject(s)
Mannitol/analogs & derivatives , Acetates/chemical synthesis , Acetylation , Benzoates/chemical synthesis , Carbohydrate Conformation , Chromatography, Gas , Chromatography, High Pressure Liquid , Isomerism , Magnetic Resonance Spectroscopy , Mannitol/chemistry , Mannitol/standards , Methylation , Molecular Structure , Oxidation-Reduction , Reference StandardsABSTRACT
Described is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-glucitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-glucitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation of the latter and acetylation yielded the desired acetates. Reported are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tetra-O-methyl derivative. Also reported for the acetates and the tetra-O-methyl derivative are their linear temperature programmed gas-liquid chromatography retention indices on three different capillary columns.
Subject(s)
Deoxyglucose/chemistry , Sorbitol/analogs & derivatives , Sorbitol/chemistry , Acetates/chemical synthesis , Acetylation , Benzoates/chemical synthesis , Carbohydrate Conformation , Chromatography, Gas , Deoxyglucose/standards , Isomerism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Methylation , Molecular Structure , Oxidation-Reduction , Reference Standards , Sorbitol/standardsABSTRACT
Described herein is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-galactitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-galactitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation yielded the desired acetates. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tetra-O-methyl derivative. Also reported for the acetates and the tetra-O-methyl derivative are their linear temperature-programmed gas-liquid chromatography retention indices on three different capillary columns.
Subject(s)
Galactitol/chemical synthesis , Acetylation , Chromatography, Gas , Chromatography, High Pressure Liquid , Galactitol/chemistry , Isomerism , Magnetic Resonance Spectroscopy , Mass Spectrometry , MethylationABSTRACT
Described herein is an efficient method for the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-fucitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-fucitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation of the latter and acetylation yielded the desired acetates. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative. Also reported for the acetates and the tri-O-methyl derivative are their linear temperature programmed gas-liquid chromatography retention indices on three different capillary columns.
