| 59964-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 59964-41-9
• 化学式: C₃₅H₃₅F₃O₈S
• 分子量: 672.719
• InChiKey: HLMXSCSCKDNBNY-BKJHVTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 四丁基碘化铵 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-[1:2,3:4]-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  没有指导基团的1,2-顺式-α-糖苷的选择性合成。在迭代寡糖合成中的应用

  摘要：

  描述了一种高选择性合成1，2-顺式-α-连接的糖苷的方法，该方法不需要使用通常用于控制非对映选择性的专门保护基图案。可以使用硫代糖苷受体，允许迭代寡糖合成。该方法消除了对具有高度专门化和非常规保护基模式的单糖进行冗长合成的需要。

  DOI：

  10.1021/ol401095k
• 作为产物：
  描述：

  苯基2,3,4,6-四-O-苄基-1-硫代-beta-D-吡喃葡萄糖苷 、 三氟甲磺酸酐 在 N-甲基马来酰亚胺 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  没有指导基团的1,2-顺式-α-糖苷的选择性合成。在迭代寡糖合成中的应用

  摘要：

  描述了一种高选择性合成1，2-顺式-α-连接的糖苷的方法，该方法不需要使用通常用于控制非对映选择性的专门保护基图案。可以使用硫代糖苷受体，允许迭代寡糖合成。该方法消除了对具有高度专门化和非常规保护基模式的单糖进行冗长合成的需要。

  DOI：

  10.1021/ol401095k

文献信息

• Why Are the Hydroxy Groups of Partially Protected <i>N</i>-Acetylglucosamine Derivatives Such Poor Glycosyl Acceptors, and What Can Be Done about It? A Comparative Study of the Reactivity of <i>N</i>-Acetyl-, <i>N</i>-Phthalimido-, and 2-Azido-2-deoxy-glucosamine Derivatives in Glycosylation. 2-Picolinyl Ethers as Reactivity-Enhancing Replacements for Benzyl Ethers
  作者：David Crich、Vadim Dudkin

  DOI：10.1021/ja010086b

  日期：2001.7.1

  Competition experiments were used to determine that the 4-OH of a 2-deoxy-2-azidoglucose derivative is more reactive than that of the corresponding N-phthalimido glucose derivative which, in turn, is more easily glycosylated than the N-acetyl derivative. Glycosylation of the C-OH groups of the N,N-diacetyl and N-acetyl-N-benzyl glucosamine was also found to be superior to that of the simple N-acetyl substance. The 3-O-picolinyl ether of a 4,6-O-benzylidene-protected N-acetylglucosamine was shown to have a strong intramolecular hydrogen bond to the adjacent acetamide group. This interaction does not persist in the 3-O-picolinyl-6-O-benzyl N-acetylglucosamine derivative. owing to a probable competing hydrogen bond between the 4-OH and the picolinyl ether. However, in the 3-O-picolinyl-4-O-benzyl N-acetylglucosamine regioisomer the picolinyl-acetamide hydrogen bond persists and leads to an enhancement of reactivity of the 6-OH, over and above that in the corresponding 3-O-benzyl ether. due to disruption of the typical intermolecular amide hydrogen bonding scheme. It is demonstrated that the picolinyl ether is readily removed by hydrogenolysis at atmospheric pressure and room temperature.
• Synthesis of a novel pentasaccharide core component from the lipooligosaccharide of Moraxella catarrhalis
  作者：Andrew G. Pearson、Ian R. Peak、Jennifer C. Wilson、I. Darren Grice

  DOI：10.1016/j.carres.2011.10.002

  日期：2011.12

  The novel pentasaccharide [p-(trifluoroacetamido)phenyl]ethyl 3-O-beta-D-glucopyranosyl-4-O-beta-D-glucopyranosyl-6-O-[2-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-alpha-D-glucopyranoside (1), which includes a linker moiety to enable facile coupling to an antigenic protein, was synthesised as a component of a potential vaccine candidate against the Gram-negative bacterium Moraxella catarrhalis. This microorganism is one of three principal causative agents of otitis media in children. The pentasaccharide represents a common cross-serotype (A, B and C) structure from the lipooligosaccharides of Moraxella catarrhalis. (C) 2011 Elsevier Ltd. All rights reserved.