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为了探讨C-糖苷高效、简便的合成方法,分别以D-核糖和2,3-O-异丙叉基-D-核糖为原料,与膦叶立德进行Wittig-Michael加成串联反应,然后不同碱处理,一锅法高产率立体专一性地合成相应的(2,3-O-异丙叉基)-β-C-D-核糖乙酸乙酯和(2,3-O-异丙叉基)-β-C-D-核糖乙酸;所得酯经DIBAL-H低温还原,得相应的核糖基醛衍生物;以D-木糖为原料,经1,2-羟基保护成缩丙酮,3,5-位二羟基三氟甲磺酰基化、叠氮化,1,2-羟基脱保护,然后经与膦叶立德Wittig-Michael加成串联反应,碱处理,高产率、立体专一性地合成了含两个叠氮基的β-C-D-核糖乙酸.提供了一种C-糖苷及氨基C-糖苷快捷、高效、简便的合成方法.化合物结构经~1H NMR、~(13)C NMR、HRMS等确证.
In order to investigate the efficient and convenient synthesis method of C-glycosides, Wittig-Michael addition series reaction of phosphine ylide with D-ribose and 2,3-O-isopropylidene-D-ribose as raw materials, (2,3-O-isopropylidene) -β-CD-ribose ethyl acetate and (2,3-O-isopropylidene) - β-CD-ribose acetic acid; the resulting ester is reduced by DIBAL-H to give the corresponding ribosyl aldehyde derivatives; D-xylose as the raw material, 1,2-hydroxy protected acetal, Hydroxy trifluoromethanesulfonylation, azidation, 1,2-hydroxy deprotection, and then with phosphine ylide Wittig-Michael addition reaction in series, alkali treatment, high yield, stereoselective synthesis of two stacks Nitrogen-based β-CD-ribose acetic acid provides a fast, efficient and convenient method for the synthesis of C-glycosides and amino C-glycosides. The structures of the compounds were confirmed by ~ 1H NMR, ~ 13 C NMR, HRMS and so on.