糖誘導体の合成並びに薬剤学的研究 (第1報)
Alkyl β-D-Xyloside類の合成
1958 年 78 巻 5 号 p. 523-526
詳細
1958 年 78 巻 5 号 p. 523-526
D-Xylose was derived to acetobromo-D-xylose, which was condensed with various aliphatic alcohols in chloroform by the König-Knorr reaction, and 10 kinds of alkyl 2, 3, 4-tri-O-acetyl-β-D-xylopyranoside were newly prepared. Butyl compound, m.p. 101.5-102.0°; pentyl, m.p. 55.0-56.5°; hexyl, syrup; octyl, syrup; decyl, m.p. 50-51°; dodecyl, m.p. 59.5-61.0°, tetradecyl, m.p. 67.5-68.5°; hexadecyl, m.p. 74-75°; octadecyl, m.p. 79-80°; cis-9-octadecenyl, b.p0.1 209°.
These xylopyranosides were deacetylated with 0.001N sodium methoxide to alkyl β-D-xylopyranosides. Butyl compound, m.p. 90.0-91.5°, or m.p. 57-58° with 1 mole of water of crystallization; pentyl, m.p. 90.0-91.5°, or m.p. 58-59° with 1 mole of water of crystallization; hexyl, m.p. 90-91°; octyl, syrup; decyl, m.p. 98.5-99.5°; dodecyl, m.p. 101.5-102°; tetradecyl, m.p. 103-104°; hexadecyl, m.p. 105.5-107.0°; octadecyl, m.p. 107-108°; cis-9-octadecenyl, syrup. Of these, purification of pentyl, octyl, and cis-9-octadecenyl β-D-xylopyranosides was difficult by the usual method that they were separated and purified through column chromatography.
