2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-biotinylamino-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylamino-octadecane-1,3,4-triol | 1176031-06-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-biotinylamino-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylamino-octadecane-1,3,4-triol
• CAS: 1176031-06-3
• 化学式: C₅₃H₉₀N₄O₁₁S
• 分子量: 991.384
• InChiKey: UPTRQCSIMGXXAY-AJMDFWEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  69.0
• 可旋转键数：
  36.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  195.17
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-biotinylamino-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylamino-octadecane-1,3,4-triol 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 C₄₅H₈₂N₄O₁₀S
  参考文献：
  名称：

  Facile synthesis of biotin-labelled α-galactosylceramide as antigen for invariant natural killer T cells

  摘要：

  When iNKT cells are stimulated by the CD1d presented exogenous alpha-galactosylceramide, a myriad of cytokines are released that trigger a variety of immune responses. However, the invisibility and poor aqueous Solubility of alpha-galactosylceramide during bioassays have rendered it difficult to study the aforementioned biological responses. Accordingly, a biotin-labelled alpha-galactosylceramide was prepared to facilitate detection of this antigen in the immune process. The problematic low solubility was also remedies via incorporation of a truncated acyl chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.007
• 作为产物：
  描述：

  2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-amino-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylaminooctadecane-1,3,4-triol 、 (+)生物素-N-琥珀酰亚胺基酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-biotinylamino-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylamino-octadecane-1,3,4-triol
  参考文献：
  名称：

  Facile synthesis of biotin-labelled α-galactosylceramide as antigen for invariant natural killer T cells

  摘要：

  When iNKT cells are stimulated by the CD1d presented exogenous alpha-galactosylceramide, a myriad of cytokines are released that trigger a variety of immune responses. However, the invisibility and poor aqueous Solubility of alpha-galactosylceramide during bioassays have rendered it difficult to study the aforementioned biological responses. Accordingly, a biotin-labelled alpha-galactosylceramide was prepared to facilitate detection of this antigen in the immune process. The problematic low solubility was also remedies via incorporation of a truncated acyl chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.007