1-Bromo-2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranoside | 220679-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Bromo-2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranoside
• 英文别名: 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl bromide；[(2R,3S,4R,5R,6R)-5-azido-6-bromo-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 220679-83-4
• 化学式: C₂₆H₃₆BrN₃O₄Si
• 分子量: 562.579
• InChiKey: USCWGNBYPAZVFL-JYSSUKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-Bromo-2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranoside 在 4 A molecular sieve 、 四丁基氟化铵 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol
  参考文献：
  名称：

  低聚糖的快速组装：布鲁氏锥虫的糖基磷脂酰肌醇锚的全合成。

  摘要：

  六个基本组成部分，六个反应步骤：最新开发的创新方法促进了复杂寡糖核心1（此处显示有保护基团）的收敛合成，从而实现了糖基磷脂酰肌醇（GPI）锚的全部合成。关键因素是通过使用1,2-二缩醛保护基调节结构单元的反应性，以及甘油和肌醇与手性双（二氢吡喃）的脱对称性。

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3423::aid-anie3423>3.0.co;2-i
• 作为产物：
  描述：

  ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 、 溴 、 双(三甲基硅烷基)氨基钾 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 55.5h， 生成 1-Bromo-2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Baeschlin, Daniel K.; Chaperon, Andre R.; Green, Luke G., Chemistry - A European Journal, 2000, vol. 6, # 1, p. 172 - 186

  摘要：

  DOI：

文献信息

• Convergent Synthesis of a Fully Phosphorylated GPI Anchor of the CD52 Antigen
  作者：Xiaoming Wu、Zhongwu Guo

  DOI：10.1021/ol701870m

  日期：2007.10.1

  A fully phosphorylated GPI anchor (1) of the CD52 antigen was synthesized by a highly convergent strategy. After a trimannose and a phospholipidated pseudodisaccharide were prepared separately, they were coupled together to form the GPI core, which was then phosphorylated to introduce two phosphoethanolamine moieties in one step to afford CD52 GPI in its fully protected form. Finally, global deprotection of the product resulted in 1.
• Synthesis and biological evaluation of sperm CD52 GPI anchor and related derivatives as binding receptors of pore-forming CAMP factor
  作者：Xiaoming Wu、Zhihong Shen、Xiangqun Zeng、Shenhui Lang、Michael Palmer、Zhongwu Guo

  DOI：10.1016/j.carres.2008.03.033

  日期：2008.7

  Sperm CD52 GPI anchor and its derivatives containing different carbohydrate chains were prepared, in a highly convergent fashion starting from the same properly protected phospholipidated pseudodisaccharide. Coupling this common key intermediate to various oligosaccharyl donors quickly afforded the framework of the synthetic targets, which was followed by global deprotection to furnish the desired structures. Preliminary studies on the biological properties of the synthetic GPI derivatives indicated that both the intact GPI anchor and the free phospholipidated pseudodisaccharide interacted strongly with CAMP factor, a pore-forming bacterial toxin. (C) 2008 Elsevier Ltd. All rights reserved.