1,2,3,4-tetra-O-trimethylsilyl-α-D-galactopyranose | 446302-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4-tetra-O-trimethylsilyl-α-D-galactopyranose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methanol
• CAS: 446302-66-5
• 化学式: C₁₈H₄₄O₆Si₄
• 分子量: 468.886
• InChiKey: AYLTXXDZXMAHBB-DISONHOPSA-N

物化性质

• 沸点：
  408.8±45.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-trimethylsilyl-α-D-galactopyranose 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到trimethylsilyl 6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

  摘要：

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

  DOI：

  10.1021/jo102064p
• 作为产物：
  描述：

  alpha-D-半乳糖 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 5.0h， 生成 1,2,3,4-tetra-O-trimethylsilyl-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents

  摘要：

  A new approach to deliver dopamine into the central nervous system, based on the use of D-glucose as transportable agent, has been studied. Glycosyl dopamine derivatives bearing the sugar moiety linked to either the amino group or the catechol ring of dopamine through amide, eater or glycosidic bonds were synthesised as potential antiparkinsonian agents. Studies on the binding to dopamine D-2 receptor, in vitro stability, and locomotive effect in mice of the synthetic glycoconjugates are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00073-2

文献信息

• Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor
  作者：Hong Wang、Yanli Cui、Rong Zou、Zhaodong Cheng、Weirong Yao、Yangyi Mao、Yongmin Zhang

  DOI：10.1016/j.carres.2016.03.019

  日期：2016.6

  been found to be very useful for the simultaneous protection of both the glycosyl donor- and the acceptor-substrates in oligosaccharide synthesis. Thus, while the per-O-trimethylsilylated glycosyl iodides served as the glycosyl donor, those bearing selectively exposed primary hydroxyl groups were found suitable as the glycosyl acceptor for the reaction. The cheap and commercially available trialkylamine

  已发现三甲基甲硅烷基（TMS）保护基对于寡糖合成中糖基供体和受体底物的同时保护非常有用。因此，尽管全-O-三甲基甲硅烷基化的糖基碘化物用作糖基供体，但发现那些带有选择性暴露的伯羟基的基团适合作为反应的糖基受体。发现便宜且可商购的三烷基胺，三乙胺是糖基化的有效促进剂。重要的是，该反应是α-立体特异性的，并且产物的产率为58％-78％。
• Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate
  作者：Yanli Cui、Zhaodong Cheng、Jianwei Mao、Yongping Yu

  DOI：10.1016/j.tetlet.2013.05.039

  日期：2013.7

  A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents
  作者：Caridad Fernández、Ofelia Nieto、Emilia Rivas、Gisela Montenegro、José A. Fontenla、Alfonso Fernández-Mayoralas

  DOI：10.1016/s0008-6215(00)00073-2

  日期：2000.8

  A new approach to deliver dopamine into the central nervous system, based on the use of D-glucose as transportable agent, has been studied. Glycosyl dopamine derivatives bearing the sugar moiety linked to either the amino group or the catechol ring of dopamine through amide, eater or glycosidic bonds were synthesised as potential antiparkinsonian agents. Studies on the binding to dopamine D-2 receptor, in vitro stability, and locomotive effect in mice of the synthetic glycoconjugates are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of a Versatile Building Block for the Preparation of 6-<i>N</i>-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids
  作者：Peter J. Jervis、Liam R. Cox、Gurdyal S. Besra

  DOI：10.1021/jo102064p

  日期：2011.1.7

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.