碘-氰基硼氢化钠介导的六吡喃糖苷 4,6-O-亚苄基缩醛的还原开环反应。
Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides.
机构信息
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, S.A.S. Nagar, Punjab, India.
出版信息
Carbohydr Res. 2010 Dec 10;345(18):2709-13. doi: 10.1016/j.carres.2010.10.013. Epub 2010 Oct 20.
A quick, efficient and convenient method for the regiospecific reductive ring opening of 4,6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides, leading to the exclusive formation of the corresponding 6-O-benzyl ethers, using sodium cyanoborohydride in the presence of molecular iodine, is reported. It has been observed that common protecting groups such as ethers and esters are well tolerated under the conditions studied. The reaction was proved unsuccessful when applied to a glucosamine-derived benzylidene acetal.
本文报道了一种快速、高效、便捷的方法，用于通过在分子碘存在下使用氰基硼氢化钠对单糖和二糖的 O-/S-烷基/芳基糖苷的 4,6-O-亚苄基缩醛进行区域选择性还原开环，从而专一地形成相应的 6-O-苄基醚。研究表明，在研究条件下，常见的保护基如醚和酯都能很好地耐受。当应用于葡萄糖胺衍生的亚苄基缩醛时，该反应被证明是不成功的。
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