allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-pyranoside | 693784-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-pyranoside
• 英文别名: allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranoside；[(2S,3S,4S,6R)-3-acetyloxy-2-methyl-6-prop-2-enoxyoxan-4-yl] acetate
• CAS: 693784-90-6
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: RLRMTMFCYKCIMT-KNDHEWATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-pyranoside 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 18.0h， 以80%的产率得到1,4-di-(3',4'-di-O-acetyl-2',6'-dideoxy-α-L-arabino-hexopyranosidly)-2-butene
  参考文献：
  名称：

  Preparation of macrocyclic 15N-labelled oligoaminodeoxysaccharides as probes for RNA-binding

  摘要：

  通过烯烃复分解和环闭合复分解反应，以1,4-丁二醇为前体，在4位和4′位上O-烯丙基化2-脱氧-L-鼠李糖醛，从而制备出两种大环氨基糖苷。为了研究溶液中与调节RNA结构的相互作用，通过核磁共振光谱法对大环的四个氨基进行了15N标记。引入15N标记的关键步骤是使用市售的15NH4OAc进行还原胺化。还原胺化具有出色的立体控制。作为副产品，分离出异常的非环状氨基腈，其来源于分子内亚胺的形成，然后氰化物加成到中间体的CN双键上。

  DOI：

  10.1039/b412436g
• 作为产物：
  描述：

  2-deoxy-3,4-di-O-acetyl-α-L-rhamnopyranose 、 烯丙醇 在 polymer-bound PPh₃*HBr 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以41%的产率得到allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-pyranoside
  参考文献：
  名称：

  Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties

  摘要：

  The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C-2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.013