n-tridecanyl α-D-galactopyranoside

• 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-tridecanyl α-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-tridecoxyoxane-3,4,5-triol
• 化学式: C₁₉H₃₈O₆
• 分子量: 362.507
• InChiKey: IEGRYKCSNXRFCZ-SPOLIRPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  十三烷醇 在 ammonium hydroxide 、 三氟化硼乙醚 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.2h， 生成 n-tridecanyl α-D-galactopyranoside
  参考文献：
  名称：

  The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

  摘要：

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.069

文献信息

• Rapid Preparation of Glycolipid Libraries by Cross Metathesis
  作者：Oliver Plettenburg、Cosina Mui、Vera Bodmer-Narkevitch、Chi-Huey Wong

  DOI：10.1002/1615-4169(200208)344:6/7<622::aid-adsc622>3.0.co;2-w

  日期：2002.8

  A new strategy for the synthesis of a well-defined glycolipid library is presented. A highly selective cross metathesis reaction is used to diversify the lipid moiety of anomerically pure alpha- or beta-glycosides, and subsequent functionalization of the double bond allows further expansion of the diversity. These glycolipids are being investigated for their effect on the immune system, especially the CD1-mediated T-cell activation.
• The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone
  作者：Shao-Xing Song、Ming-Li Wu、Xiao-Peng He、Yu-Bo Zhou、Li Sheng、Jia Li、Guo-Rong Chen

  DOI：10.1016/j.bmcl.2012.01.069

  日期：2012.3

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.