Synthesis of α-Cyclooctyl- and α-Cyclopentadecylglycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine

被引：0
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作者：
A. E. Zemlyakov
V. V. Tsikalov
V. N. Tsikalova
机构：
[1] V. I. Vernadsky Crimean Federal University,
来源：
Chemistry of Natural Compounds | 2018年 / 54卷
关键词：
-acetylglucosamine glycosides; glucosaminides muramyl dipeptide; muramyl-dipeptide glycosides;
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摘要：
N-Acetylmuramyl-L-alanyl-D-isoglutamine α-cyclooctyl- and α-cyclopentadecylglycosides were synthesized. The starting peracetylated α-N-glucosaminides were synthesized by reacting the cycloalkanols with peracetyl α-D-glucosaminyl chloride in the presence of Hg(II) iodide in CH3NO2 with heating or by using ZnCl2/tetrabutylammonium bromide in CH2Cl2 at room temperature. Sequential deacetylation, isopropyl protection, and alkylation by (S)-2-bromopropanoic acid gave α-cycloalkyl-4,6-O-isopropylidene-N-acetyl-D-muramic acids, condensation of which with the benzyl ester of L-Ala-D-iGln using the HOSu/DCC method and deprotection afforded the target glycopeptides.
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页码：1139 / 1142
页数：3
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