1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-L-galactopyranose | 1402430-22-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-L-galactopyranose
• 英文别名: [(2S,3S,4S,5S,6S)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate
• CAS: 1402430-22-1
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: QKGHBQJLEHAMKJ-PDWCTOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-L-galactal 在 sodium azide 、 ammonium cerium (IV) nitrate 、 sodium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以27.273%的产率得到
  参考文献：
  名称：

  Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations

  摘要：

  12-O-beta-D-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for the FLAG-tagging of JAG target. We synthesized four hybrid-type JAG-CMP stereoisomers (7, ent-7, 8, and ent-8), which are composed of (-)-12-OH-JA (2)/D-galactopyranoside, (-)-2/L-galactopyranoside, (+)-ent-2/D-galactopyranoside, and (+)-ent-2/L-galactopyranoside moieties, respectively, and we examined their biological features, such as the stereospecific induction of shrinkage, rate of the cellular response, and dependence on potassium channel activity. These features of the JAG-CMPs were completely consistent with those of the original JAG. These results indicate the biological equivalence of JAG and the JAG-CMPs. During the course of such biological evaluations, it was revealed that the biological activity of the CMPs is greatly dependent on the D/L-stereochemistry of a glycon moiety. To the best of our knowledge, this is the first study suggesting that the D/L-stereochemistry of the glycon moiety significantly affects the biological activity of the associated glycoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.003

文献信息

• A stereoselective and flexible synthesis to access both enantiomers of <i>N</i>-acetylgalactosamine and peracetylated <i>N</i>-acetylidosamine
  作者：Bettina Riedl、Walther Schmid

  DOI：10.3762/bjoc.14.71

  日期：——

  the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).

  合成N-乙酰半乳糖胺（GalNAc）的方法引起了极大的兴趣，因为该化合物在细胞间相互作用和受体诱导的细胞信号转导中起着举足轻重的作用。在本文中，我们提出了一种合成途径，其中目标化合物中存在的四个立体异构中心中的两个源自对映体纯的酒石酸，后者被选择性地转化为环氧醇。关键步骤是Pd催化的立体和区域选择性环氧化物的开环以及随后叠氮化物官能团的亲核取代。该方法能够合成天然D-和非天然L-构型的GalNAc，以及在很大程度上未知的N-乙酰氨基胺（IdoNAc）的两种对映异构体。