试剂控制合成抗生素沙可米星 B 的支化三糖片段。
Reagent-Controlled Synthesis of the Branched Trisaccharide Fragment of the Antibiotic Saccharomicin B.
机构信息
Department of Chemistry , Tufts University , 62 Talbot Avenue , Medford , Massachusetts 02155 , United States.
出版信息
Org Lett. 2018 Jun 1;20(11):3413-3417. doi: 10.1021/acs.orglett.8b01355. Epub 2018 May 23.
Abstract
A concise synthesis of a branched trisaccharide, α-l-Dig-(1 → 3)-[α-l-Eva-(1 → 4)]-β-d-Fuc, corresponding to saccharomicin B, has been developed via reagent-controlled α-selective glycosylations. Starting from the d-fucose acceptor, l- epi-vancosamine was selectively installed using 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropene-1-thione/oxalyl bromide mediated dehydrative glycosylation. Following deprotection, l-digitoxose was installed using the AgPF/TTBP thioether-activation method to produce the trisaccharide as a single α-anomer. This highly functionalized trisaccharide can potentially serve as both a donor and an acceptor for the total synthesis of the antibiotic saccharomicin B.
摘要
一种支化三糖，α-l-Dig-(1 → 3)-[α-l-Eva-(1 → 4)]-β-d-Fuc，对应于沙卡霉素 B，已通过试剂控制的 α-选择性糖基化方法进行了简明合成。从 d-岩藻糖受体开始，使用 2,3-双（2,3,4-三甲氧基苯基）环丙烯-1-硫酮/草酰溴介导的脱水糖基化反应，选择性地安装了 l-表坎诺胺。脱保护后，使用 AgPF/TTBP 硫醚活化法安装 l- 洋地黄糖，生成作为单一 α-异构体的三糖。这种高度官能化的三糖可作为抗生素沙卡霉素 B 全合成的供体和受体。
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