2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-azido-α-D-galactopyranosyl (1,1)-trichloroacetimide | 1176030-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-azido-α-D-galactopyranosyl (1,1)-trichloroacetimide
• 英文别名: [(3aS,4R,6R,7R,7aS)-4-(azidomethyl)-7-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl] 2,2,2-trichloroethanimidate
• CAS: 1176030-82-2
• 化学式: C₁₉H₂₃Cl₃N₄O₆
• 分子量: 509.774
• InChiKey: IUMSLUCINIFXMT-LYYZXLFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-azido-α-D-galactopyranosyl (1,1)-trichloroacetimide 、 (2S,3S,4R)-2-(N-octanoylamino)-3,4-di-O-benzoyl-1,3,4-octadecanetriol 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以55%的产率得到2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-azido-α-D-galactopyranosyl-(1,1)-(2S,3S,4R)-2-octanoylamino-3,4-O-dibenzoyl-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
• 作为产物：
  描述：

  、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-6-deoxy-6-azido-α-D-galactopyranosyl (1,1)-trichloroacetimide
  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

文献信息

• Facile synthesis of biotin-labelled α-galactosylceramide as antigen for invariant natural killer T cells
  作者：Chengfeng Xia、Wenpeng Zhang、Yalong Zhang、Robert L. Woodward、Jinhua Wang、Peng G. Wang

  DOI：10.1016/j.tet.2009.06.007

  日期：2009.8

  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.