methyl 2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranuronate | 727991-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranuronate
• 英文别名: (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-α-D-glucopyranosyluronate) trichloroacetimidate；methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-α-D-glucopyranosyluronate trichloroacetimidate；methyl (2S,3S,4R,5R,6R)-4,5-dibenzoyloxy-3-[tert-butyl(dimethyl)silyl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS: 727991-10-8
• 化学式: C₂₉H₃₄Cl₃NO₉Si
• 分子量: 675.035
• InChiKey: MLINEEZRYIJPDZ-KUMDOQPPSA-N

物化性质

• 沸点：
  615.8±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranuronate 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 水 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate
  参考文献：
  名称：

  A Chondroitin Sulfate Small Molecule that Stimulates Neuronal Growth

  摘要：

  Chondroitin sulfate glycosaminoglycans are sulfated polysaccharides involved in cell division, neuronal development, and spinal cord injury. Here, we report the synthesis and identification of a chondroitin sulfate tetrasaccharide that stimulates the growth and differentiation of neurons. These studies represent the first, direct investigations into the structure-activity relationships of chondroitin sulfate using homogeneous synthetic molecules and define a tetrasaccharide as a minimal motif required for activity.

  DOI：

  10.1021/ja0484045
• 作为产物：
  描述：

  三氯乙腈 、 5-(tert-butyldimethylsilyloxy)-2-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate 在 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以95%的产率得到methyl 2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranuronate
  参考文献：
  名称：

  [EN] SMALL MOLECULE STIMULATORS OF NEURONAL GROWTH
  [FR] PETITS STIMULATEURS DE MOLECULES DE CROISSANCE NEURONALE

  摘要：

  公开号：

  WO2005118609A3

文献信息

• Synthesis of 13C-labeled and functionalized Hyaluronan derivatives for biophysical studies and surface modifications
  作者：Stephan Rigol、Liang Xia、Athanassios Giannis

  DOI：10.1016/j.bmc.2012.11.025

  日期：2013.2

  A convergent synthesis of a tetrasaccharide partial sequence of C-13-labeled Hyaluronan is presented. This tetrasaccharide can be used for biophysical studies as well as for surface modifications. Furthermore, tetrasaccharide 7 can be employed for the synthesis of additionally labeled higher oligomers of Hyaluronan on the basis of the presented methodology. (C) 2012 Elsevier Ltd. All rights reserved.
• A Chondroitin Sulfate Small Molecule that Stimulates Neuronal Growth
  作者：Sarah E. Tully、Ross Mabon、Cristal I. Gama、Sherry M. Tsai、Xuewei Liu、Linda C. Hsieh-Wilson

  DOI：10.1021/ja0484045

  日期：2004.6.1

  Chondroitin sulfate glycosaminoglycans are sulfated polysaccharides involved in cell division, neuronal development, and spinal cord injury. Here, we report the synthesis and identification of a chondroitin sulfate tetrasaccharide that stimulates the growth and differentiation of neurons. These studies represent the first, direct investigations into the structure-activity relationships of chondroitin sulfate using homogeneous synthetic molecules and define a tetrasaccharide as a minimal motif required for activity.
• [EN] SMALL MOLECULE STIMULATORS OF NEURONAL GROWTH<br/>[FR] PETITS STIMULATEURS DE MOLECULES DE CROISSANCE NEURONALE
  申请人：CALIFORNIA INST OF TECHN

  公开号：WO2005118609A3

  公开（公告）日：2006-06-08