8-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-octanoic acid | 865775-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-octanoic acid
• 英文别名: 9-oxo-9-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]nonanoic acid
• CAS: 865775-52-6
• 化学式: C₁₅H₂₇NO₈
• 分子量: 349.381
• InChiKey: CJJYBQHXPNBJQL-FDHZTJNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  全氨基倍他环糊精 、 8-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-octanoic acid 在 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到per-6-[9-(β-D-galactopyranosylamino)-1,9-dioxononyl]amino-6-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae

  摘要：

  The use of coupling saccharide antenna onto cyclodextrins allows mobility for the biologically active galactose head group, and allows the recognition process by the lectin (KbCWL). This paper reports a chemical synthesis of beta-CD derivatives using spacer arms 3, 4, 5, 6 and 9 carbon atoms. Preliminary results suggested that recognition is strongly dependent on the length of the spacer chain between the cyclodextrin and the sugar head group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10033-8
• 作为产物：
  描述：

  8-((2R,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-octanoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 8-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-octanoic acid
  参考文献：
  名称：

  Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognisable galactosyl antenna

  摘要：

  The synthesis of a mono-galactosylated amphiphilic beta-cyclodextrin, in five steps from mono-6-azido-6-deoxy-beta-cyclodextrin, via coupling to a N-beta-D-galactopyranosylamino-antenna is described. Both characterization by electrospray mass spectrometry and NMR show the presence of only the mono-substituted product. The Langmuir isotherms of the final product and intermediates are described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.054

文献信息

• Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognisable galactosyl antenna
  作者：Alain Salameh、Adina N. Lazar、Anthony W. Coleman、Hélène Parrot-Lopez

  DOI：10.1016/j.tet.2005.06.054

  日期：2005.9

  The synthesis of a mono-galactosylated amphiphilic beta-cyclodextrin, in five steps from mono-6-azido-6-deoxy-beta-cyclodextrin, via coupling to a N-beta-D-galactopyranosylamino-antenna is described. Both characterization by electrospray mass spectrometry and NMR show the presence of only the mono-substituted product. The Langmuir isotherms of the final product and intermediates are described. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae
  作者：Rima Kassab、Caroline Felix、Hélène Parrot-Lopez、Roger Bonaly

  DOI：10.1016/s0040-4039(97)10033-8

  日期：1997.10

  The use of coupling saccharide antenna onto cyclodextrins allows mobility for the biologically active galactose head group, and allows the recognition process by the lectin (KbCWL). This paper reports a chemical synthesis of beta-CD derivatives using spacer arms 3, 4, 5, 6 and 9 carbon atoms. Preliminary results suggested that recognition is strongly dependent on the length of the spacer chain between the cyclodextrin and the sugar head group. (C) 1997 Elsevier Science Ltd.