Allyl 3,4-di-O-acetyl-2-deoxy-β-L-fucopyranoside | 245416-68-6

• 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-deoxy-β-L-fucopyranoside
• 英文别名: allyl 3,4-di-O-acetyl-2,6-dideoxy-β-L-lyxo-hexopyranoside
• CAS: 245416-68-6
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: RLRMTMFCYKCIMT-ZBPZKIAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Allyl 3,4-di-O-acetyl-2-deoxy-β-L-fucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 12.0h， 生成 Allyl 2-deoxy-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures

  摘要：

  DOI：

  10.1055/s-1999-3651
• 作为产物：
  描述：

  (2S,3R,4S)-4,6-bis(acetyloxy)-2-methyloxan-3-yl acetate 、 烯丙醇 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 Allyl 3,4-di-O-acetyl-2-deoxy-α-L-fucopyranoside 、 Allyl 3,4-di-O-acetyl-2-deoxy-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures

  摘要：

  DOI：

  10.1055/s-1999-3651

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.