Lüning B, Norberg T, Tejbrant J
Department of Organic Chemistry, University of Stockholm, Sweden.
Glycoconj J. 1989;6(1):5-19. doi: 10.1007/BF01047886.
N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carrying O-glycosidically alpha- or beta-linked peracetylated beta-D-Galp-(1-3)-D-GalNAcp carbohydrate chains, were prepared. These derivatives are intended for use in solid phase glycopeptide synthesis. Suitably protected mono- and disaccharide thioglycosides were used as carbohydrate intermediates. These were activated by treatment with bromine to give the glycosyl bromides, which were then used in silver triflate-promoted glycosidations of N-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids.
制备了N-芴甲氧羰基保护的丝氨酸和苏氨酸衍生物，它们带有通过O-糖苷键连接的α-或β-连接的全乙酰化β-D-半乳糖-(1-3)-D-氨基半乳糖碳水化合物链。这些衍生物旨在用于固相糖肽合成。适当保护的单糖和二糖硫苷用作碳水化合物中间体。通过用溴处理将它们活化以得到糖基溴，然后将其用于三氟甲磺酸银促进的N-芴甲氧羰基氨基酸苯甲酰酯的糖基化反应。用锌除去苯甲酰酯得到目标游离酸。
