N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp. 47, Moscow, Russian Federation.
Carbohydr Res. 2010 Apr 19;345(6):721-30. doi: 10.1016/j.carres.2010.01.005. Epub 2010 Jan 18.
N,N-Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles to give the corresponding alpha-glycosyl phosphate, beta-glycosyl dibenzyl phosphate, alpha-glycosyl azide, alpha-phenyl thioglycoside and alpha-glycosyl xanthate in 65-82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with alpha-configuration and highly efficient synthesis of beta-configured sialic acid glycosyl dibenzyl phosphate.
N,N-二乙酰神经氨酸氯首次被制备出来，并与各种亲核试剂反应，以 65-82%的产率和高立体选择性得到相应的α-糖苷磷酸酯、β-糖苷二苄基磷酸酯、α-糖苷叠氮化物、α-苯硫基糖苷和α-糖苷黄原酸酯，而其与简单醇的反应则没有立体选择性。新型唾液酸供体使得首次以α-构型立体选择性合成唾液酸糖苷磷酸酯和高效合成β-构型唾液酸糖苷二苄基磷酸酯成为可能。
