Blazis V J, Hawkins E S, Baker D C
Department of Chemistry, University of Tennessee, Knoxville 37996-1600.
Carbohydr Res. 1994 Feb 3;253:225-33. doi: 10.1016/0008-6215(94)80067-7.
A series of 3-C-alkyl-2,3-dideoxy-5-O-trityl-D-erythro-pentono-1,4-lactones were detritylated. The resultant free-hydroxy compounds were converted to their respective 2-C-alkyl-2,3-dideoxy-alpha,beta-L-glycero-tetrurono-1,4-lactones (L-sugar numbering) in a one-vessel reaction sequence of (a) conversion of the lactones to their aldonic acid sodium salts, (b) cleavage of the resulting aldonates with sodium metaperiodate, and (c) acidification, followed by acetylation, to give the title compounds. The unsubstituted tetrurono-1,4-lactones were inhibitory toward L1210 leukemia cells at concentrations in the 10(-4) M range.
一系列3-C-烷基-2,3-二脱氧-5-O-三苯甲基-D-赤藓戊糖-1,4-内酯被脱去三苯甲基。所得的游离羟基化合物在一个单容器反应序列中被转化为各自的2-C-烷基-2,3-二脱氧-α,β-L-甘油四糖醛酸-1,4-内酯（L-糖编号），该反应序列包括：(a) 将内酯转化为其醛糖酸钠盐；(b) 用偏高碘酸钠裂解所得的醛糖酸盐；(c) 酸化，随后乙酰化，得到标题化合物。未取代的四糖醛酸-1,4-内酯在10⁻⁴ M范围内的浓度对L1210白血病细胞具有抑制作用。
