(2'S,3'S,4'R)-7-(4'-O-hexacosanoyl-D-ribo-tetradecyl)-ethane α-C-D-galactopyranoside | 1301629-48-0

• 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: (2'S,3'S,4'R)-7-(4'-O-hexacosanoyl-D-ribo-tetradecyl)-ethane α-C-D-galactopyranoside
• 英文别名: [(3S,4S,5R)-3,4-dihydroxy-1-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]nonadecan-5-yl] hexacosanoate
• CAS: 1301629-48-0
• 化学式: C₅₁H₁₀₀O₉
• 分子量: 857.35
• InChiKey: ZIBRSKCFFDSJEH-XHSUSRKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  60
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-trimethylsilylacetylene)-D-ribo-butan-1-ol 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 氟化铵 、 正丁基锂 、 草酰氯 、 蜡酸 、 sodium acetate 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 对甲苯磺酰肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.17h， 生成 (2'S,3'S,4'R)-7-(4'-O-hexacosanoyl-D-ribo-tetradecyl)-ethane α-C-D-galactopyranoside
  参考文献：
  名称：

  Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000

  摘要：

  Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.044

文献信息

• Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000
  作者：Aline Banchet-Cadeddu、Agathe Martinez、Stéphane Guillarme、Véronique Parietti、Fanny Monneaux、Eric Hénon、Jean-Hugues Renault、Jean-Marc Nuzillard、Arnaud Haudrechy

  DOI：10.1016/j.bmcl.2011.02.044

  日期：2011.4

  Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests. (C) 2011 Elsevier Ltd. All rights reserved.