N-[2-(β-D-galactopyranosyloxy)ethyl]octadecanoylamide | 483362-39-6

• 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: N-[2-(β-D-galactopyranosyloxy)ethyl]octadecanoylamide
• 英文别名: N-[2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]octadecanamide
• CAS: 483362-39-6
• 化学式: C₂₆H₅₁NO₇
• 分子量: 489.693
• InChiKey: HRTYFECXABFHQW-MMXJFWRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-[2-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)ethyl]octadecanoylamide 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 N-[2-(β-D-galactopyranosyloxy)ethyl]octadecanoylamide
  参考文献：
  名称：

  NOVEL GALACTOSYLCERAMIDE ANALOGS AND BETA-GLUCOCEREBROSIDASE ACTIVATORS,EXTERNAL SKIN PREPARATIONS AND METHOD OF ACTIVATING BETA-GLUCOCEREBROSIDASE USING THE ANALOGS

  摘要：

  公开号：

  EP1408045B1

文献信息

• Direct and Efficient Glycosylation Protocol for Synthesizing α-Glycolipids: Application to the Synthesis of KRN7000
  作者：Omar Boutureira、José Antonio Morales-Serna、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1002/ejoc.200701228

  日期：2008.4

  biologically active galactosyl ceramide KRN7000 and other α-glycolipids with excellent yield and stereoselectivity by using per-O-silylated galactosyl iodide and stannyl ethers as glycosylation partners. This direct glycosylation reaction reduces the overall number of steps and provides rapid access to biologically important α-galactosyl ceramide derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  在此，我们描述了一种简单实用的协议，用于通过使用过 O-甲硅烷基化半乳糖基碘和甲锡醚作为糖基化伙伴，以优异的产量和立体选择性获取生物活性半乳糖神经酰胺 KRN7000 和其他 α-糖脂。这种直接的糖基化反应减少了总步骤数，并提供了对生物学上重要的 α-半乳糖神经酰胺衍生物的快速获取。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Novel galactosylceramide analogs, and beta-glucocerebrosidase activators, external skin preparations and method of activating beta-glucocerebrosidase using the analogs
  申请人：——

  公开号：US20040242499A1

  公开（公告）日：2004-12-02

  Galactosylceramide analogues represented by the following formula (1) or (2). 1 (wherein X and Y each represent S or O, R 1 and R 2 each represent an alkyl group or an alkenyl group each having 9 to 35 carbon atoms. R 3 represents an alkyl group or an alkenyl group each having 2 to 30 carbon atoms.) It is provided a &bgr;-glucocerebrosidase activator which is easily available, and external skin preparations and a method of activating &bgr;-glucocerebrosidase, in which improvement in formation of horny layer transmission barrier is expected by activating &bgr;-glucocerebrosidase so that an improved effect in rough skin is also expected.

  提供以下公式（1）或（2）所表示的类似半乳糖鞘氨醇： 其中，X和Y各代表S或O，R1和R2各代表一个有9到35个碳原子的烷基或烯基，R3代表一个有2到30个碳原子的烷基或烯基。提供了一种易于获取的β-葡糖鞘脂酶激活剂，以及激活β-葡糖鞘脂酶的外用皮肤制剂和方法，通过激活β-葡糖鞘脂酶，预期改善角质层传递屏障的形成，从而也预期改善皮肤粗糙的效果。
• Novel galactosylceramide analogues, and beta-glucocerebrosidase activator, external skin preparations and method of activating beta-glucocerebrosidase using the same
  申请人：Uematsu Rie

  公开号：US20070111951A1

  公开（公告）日：2007-05-17

  Galactosylceramide analogues represented by the following formula (1) or (2). (wherein X and Y each represent S or O, R 1 and R 2 each represent an alkyl group or an alkenyl group each having 9 to 35 carbon atoms. R 3 represents an alkyl group or an alkenyl group each having 2 to 30 carbon atoms.) It is provided a β-glucocerebrosidase activator which is easily available, and external skin preparations and a method of activating β-glucocerebrosidase, in which improvement in formation of horny layer transmission barrier is expected by activating β-glucocerebrosidase so that an improved effect in rough skin is also expected.
• US7183261B2
  申请人：——

  公开号：US7183261B2

  公开（公告）日：2007-02-27
• NOVEL GALACTOSYLCERAMIDE ANALOGS AND BETA-GLUCOCEREBROSIDASE ACTIVATORS,EXTERNAL SKIN PREPARATIONS AND METHOD OF ACTIVATING BETA-GLUCOCEREBROSIDASE USING THE ANALOGS
  申请人：KAO CORPORATION

  公开号：EP1408045B1

  公开（公告）日：2009-05-27