A Reinvestigation of the Tritylation of Maltose

概要

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Treatment of β-maltose with 2 molar equivalents of trityl chloride in pyridine at 100℃ for 1 h afforded trityl 6,6'-di-O-trityl-β-maltoside (1), 2,6'-di-O-trityl-α-maltose (2), trityl 6'-O-trityl-β-maltoside (3), 6,6'-di-O-tritylmaltose (4), and a mixture of 6-and 6'-O-tritylmaltoses (6). The ratios of 1,2,3,and 6 to the main product, 4 were estimated to be 6,9,11,and 31 : 100,respectively, by thin-layer chromatogram spectrophotometry at 260 nm. Each trityl ether was isolated by column chromatography (CC) and then acetylated individually. After acetylation, 6 was separated by CC to give 6-O-tritylmaltose heptaacetate (6A) and 6'-O-tritylmaltose heptaacetate (7A). The structures of all trityl ethers were established by means of ^1H-nuclear magnetic resonance (NMR) and ^<13>C-NMR analyses, optical rotation measurements, etc. The trityl ethers of maltose were compared with those of cellobiose, and the relationship between their conformations and their reactivities or chromatographic behavior is discussed.
公益社団法人日本薬学会の論文
1983-04-25