octyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside | 368870-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: octyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-octoxy-6-(trityloxymethyl)oxan-3-yl]acetamide
• CAS: 368870-54-6
• 化学式: C₃₅H₄₅NO₆
• 分子量: 575.745
• InChiKey: BOSFJBSEGRPZPC-NEPHXMAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside 在 palladium on activated charcoal 硫酸 、 氢气 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.17h， 生成 octyl 2-acetamido-2-deoxy-6-O-[2,2-bis(hydroxymethyl)-3-hydroxypropyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Central Neural Tumor Destruction by Controlled Release of a Synthetic Glycoside Dispersed in a Biodegradable Polymeric Matrix

  摘要：

  An octyl N-acetylglucosaminide derivative with a pentaerythritol chain at position 6 has been synthesized and evaluated as an inhibitor of neural tumor growth. The glycoside inhibited the growth of a neuroectodermic tumor implanted in rats and, when loaded on a slow-delivery polymer disk, caused the destruction of cultured human astroblastoma obtained after surgical biopsy.

  DOI：

  10.1021/jm025620k
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 反应 4.5h， 生成 octyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside
  参考文献：
  名称：

  Central Neural Tumor Destruction by Controlled Release of a Synthetic Glycoside Dispersed in a Biodegradable Polymeric Matrix

  摘要：

  An octyl N-acetylglucosaminide derivative with a pentaerythritol chain at position 6 has been synthesized and evaluated as an inhibitor of neural tumor growth. The glycoside inhibited the growth of a neuroectodermic tumor implanted in rats and, when loaded on a slow-delivery polymer disk, caused the destruction of cultured human astroblastoma obtained after surgical biopsy.

  DOI：

  10.1021/jm025620k

文献信息

• Synthesis of a tetrasaccharide related to the repeating unit of the O-antigen from Escherichia coli K-12
  作者：Bimalendu Roy、Robert A. Field、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2009.09.026

  日期：2009.11

  Synthesis of a tetrasaccharide related to the repeating unit of the O-antigen from Escherichia coli K-12 is reported in the form of its octyl glycoside. Syntheses of the 1,2-cis glycosidic linkages have been accomplished by using NIS in conjunction with H(2)SO(4)-silica, and it was found to be stereoselective and productive. The synthesized tetrasaccharide will be utilized as the substrate for gal

  以其辛基糖苷的形式报道了从大肠杆菌K-12合成与O-抗原的重复单元有关的四糖。1,2-顺式糖苷键的合成已通过使用NIS结合H（2）SO（4）-二氧化硅来完成，并且被发现具有立体选择性和生产性。合成的四糖将用作半乳糖呋喃糖基转移酶WbbI的底物。