(2R,4aR,6R,7R,8R,8aS)-7-amino-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol | 1314535-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6R,7R,8R,8aS)-7-amino-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 1314535-79-9
• 化学式: C₁₈H₂₉NO₅Si
• 分子量: 367.517
• InChiKey: XIACMDFHVGFORY-TYENPDHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6R,7R,8R,8aS)-7-amino-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,3,5-三苯基-1H-吡唑 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 水 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of d -glucose

  摘要：

  2-NBDG is a widely used fluorescent tracer for monitoring D-glucose uptake into single living cells. However, 2-NBDG alone is not sufficient for monitoring the net stereoselective uptake of D-glucose, unless its possible non-stereoselective uptake is properly evaluated. L-Glucose derivatives, which emit fluorescence distinct from that of 2-NBDG, should provide valuable information on the stereoselective uptake, when used with 2-NBDG in combination. In the present study, we synthesized Texas Red (sulforhodamine 101 acid)-coupled and [2-(benz-2-oxa-1,3-diazol-4-yl)amino]-coupled 2-deoxy-D-glucose, referred to as [2-TRG] and [2-BDG], respectively. These derivatives showed emission wavelength longer and shorter than that of 2-NBDG, respectively. 2-TRLG, an antipode of 2-TRG, proved to be an effective tracer for evaluating the extent of non-stereoselective uptake of 2-NBDG when used simultaneously with 2-NBDG. On the other hand, 2-BDG exhibited very weak fluorescence, but the application of a novel cross coupling in the presence of a benzoxadiazole group may be useful for the future development of effective glucose tracers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.148
• 作为产物：
  描述：

  2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 2,4,6-三甲基吡啶 、 甲醇 、 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4aR,6R,7R,8R,8aS)-7-amino-2-phenyl-6-(2-(trimethylsilyl)ethoxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol
  参考文献：
  名称：

  Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of d -glucose

  摘要：

  2-NBDG is a widely used fluorescent tracer for monitoring D-glucose uptake into single living cells. However, 2-NBDG alone is not sufficient for monitoring the net stereoselective uptake of D-glucose, unless its possible non-stereoselective uptake is properly evaluated. L-Glucose derivatives, which emit fluorescence distinct from that of 2-NBDG, should provide valuable information on the stereoselective uptake, when used with 2-NBDG in combination. In the present study, we synthesized Texas Red (sulforhodamine 101 acid)-coupled and [2-(benz-2-oxa-1,3-diazol-4-yl)amino]-coupled 2-deoxy-D-glucose, referred to as [2-TRG] and [2-BDG], respectively. These derivatives showed emission wavelength longer and shorter than that of 2-NBDG, respectively. 2-TRLG, an antipode of 2-TRG, proved to be an effective tracer for evaluating the extent of non-stereoselective uptake of 2-NBDG when used simultaneously with 2-NBDG. On the other hand, 2-BDG exhibited very weak fluorescence, but the application of a novel cross coupling in the presence of a benzoxadiazole group may be useful for the future development of effective glucose tracers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.148

文献信息

• Syntheses of N -aryl-protected glucosamines and their stereoselectivity in chemical glycosylations
  作者：Yuji Otsuka、Toshihiro Yamamoto、Koichi Fukase

  DOI：10.1016/j.tetlet.2017.06.037

  日期：2017.8

  to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β

  将N-芳基保护基引入葡糖胺中以实现β-选择性糖基化。通过布赫瓦尔德-哈特维格反应合成了各种N-芳基氨基糖。在三甲基甲硅烷基三氟甲磺酸酯存在下，使用N-芳基氨基糖的糖基三氯乙亚氨酸酯进行的糖基化顺利进行。包含供电子的2，4-二甲氧基苯基（DMP）基团的糖基供体的使用导致糖基化以高β选择性进行。这种立体选择性似乎源于氮丙啶中间体的形成。DMP保护基可通过使用六氰基乙酸铵（IV）立即去除。