A facile method for the synthesis of partially O-methylated alditol acetate standards for GC–MS analysis of galactofuranose-containing structures

• Published in: Carbohydrate research 2013-09, Vol.379, p.18-20
• Main Authors: He, Jian-yu, Guo, Yu-na, Zhang, Ling-ling, Huang, Lin-hong
• Format: Article
• Language: English
• Subjects: acetates; Acetates - chemical synthesis; Acetates - chemistry; barium; Carbohydrate Conformation; ethers; Galactofuranose-containing structures; Galactose - analogs & derivatives; Galactose - chemistry; Gas Chromatography-Mass Spectrometry; GC–MS standards; glycosides; Hydrochloric Acid - chemistry; Methylation; Methylation analysis; Partially O-methylated alditol acetates; Sugar Alcohols - chemical synthesis; Sugar Alcohols - chemistry
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2013.06.005

EIMS of partially O-methylated alditol acetate derivatives obtained mainly from methyl galactofuranoside. [Display omitted] •Galactose was processed into methyl galactofuranoside.•Mixtures of partially O-methylated alditol acetate standards (PMAAs) were synthesized.•The PMAAs could be used as GC–MS standards for identification of galactofuranoside. Mixtures of partially O-methylated alditol acetate standards of galactofuranose were synthesized rapidly. Methyl galactofuranosides were obtained with a yield of 79.9% within 4h under optimized reaction conditions. Methylation of methyl glycosides was carried out in the presence of BaO/Ba(OH)2·8H2O, giving rise to mixtures of partially methylated glycosides. The batch containing the most diverse structures of methyl ethers was converted into partially O-methylated alditol acetates (PMAAs) and then subjected to GC–MS. These PMAAs could be used as GC–MS standards for simultaneous identification of galactofuranose units with diverse linkages in complex carbohydrates.