Department of Chemistry, University of Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada.
INRS-Institut Armand-Frappier, Université du Québec, 531 boul. des Prairies, Laval, QC H7V 1B7, Canada.
Molecules. 2020 Dec 29;26(1):115. doi: 10.3390/molecules26010115.
Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per--acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the position of the aromatic residue. The corresponding unprotected lactosides, obtained by Zemplén transesterification, were regioselectively 3'--sulfated using tin chemistry activation followed by treatment with sulfur trioxide-trimethylamine complex (MenN-SO). Additional derivatives were also prepared from the vanillin's aldehyde using a Knoevenagel reaction to provide extended α, β-unsaturated carboxylic acid which was next reduced to the saturated counterpart.
采用相转移催化反应，从全乙酰化乳酰溴合成了基于香草醛的乳糖苷衍生物。然后修饰香草醛部分的醛基，生成一系列在芳基残基的 位具有可变官能团的相关类似物。通过 Zemplén 酯交换获得的相应非保护的乳糖苷，通过锡化学活化进行选择性 3'-硫酸化，然后用三氧化硫-三甲胺复合物（MenN-SO）处理。还可以使用 Knoevenagel 反应从香草醛的醛基制备其他衍生物，以提供扩展的α，β-不饱和羧酸，然后将其还原为相应的饱和羧酸。
