1,4-di(2',6'-dideoxy-α-L-arabino-pyranosyl)-1,4-butanediol | 693784-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di(2',6'-dideoxy-α-L-arabino-pyranosyl)-1,4-butanediol
• 英文别名: 1,4-di-(2',6'-dideoxy-α-L-arabino-hexopyranosyl)-butane；(2S,3R,4S,6R)-6-[4-[(2R,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxybutoxy]-2-methyloxane-3,4-diol
• CAS: 693784-98-4
• 化学式: C₁₆H₃₀O₈
• 分子量: 350.409
• InChiKey: NMNZCPQNDFULRG-UFTFSBDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-di(2',6'-dideoxy-α-L-arabino-pyranosyl)-1,4-butanediol 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.08h， 生成 1,4-di-(4'-O-allyl-2',6'-dideoxy-3'-oxo-α-L-arabino-pyranosyl)-1,4-butanediol
  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：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 Grubbs catalyst first generation 、 platinum(IV) oxide amberlite A-26 (OH(-) form) 、 polymer-bound PPh₃*HBr 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 20.0~40.0 ℃ 、100.0 kPa 条件下， 反应 78.0h， 生成 1,4-di(2',6'-dideoxy-α-L-arabino-pyranosyl)-1,4-butanediol
  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

文献信息

• Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties
  作者：Andreas Kirschning、Guang-wu Chen、Janis Jaunzems、Martin Jesberger、Markus Kalesse、Meike Lindner

  DOI：10.1016/j.tet.2004.02.013

  日期：2004.4

  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.
• Preparation of macrocyclic 15N-labelled oligoaminodeoxysaccharides as probes for RNA-binding
  作者：Janis Jaunzems、Benjamin Oelze、Andreas Kirschning

  DOI：10.1039/b412436g

  日期：——

  Two macrocyclic aminoglycosides were prepared from a 1,4-butanediol linked 2-deoxy-L-rhamnal which was O-allylated at the 4- and 4′-positions via the precursor allyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexoside employing olefin metathesis and ring closing metathesis in a sequential manner. The macrocycles were 15N-labelled at all four amino groups in order to study interactions with regulatory RNA structures in solution by NMR spectroscopy. A key step for the introduction of the 15N-label was a reductive amination step using commercially available 15NH4OAc. The reductive amination proceeds with excellent stereocontrol. As a by-product the unusual acyclic amino nitrile was isolated which originated from intramolecular imine formation followed by cyanide addition to the intermediate CN double bond.

  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。