methyl 3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-α-D-ribo-hexopyranoside | 833460-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-α-D-ribo-hexopyranoside
• 英文别名: [(2R,3S,4S,6S)-4-azido-6-methoxy-3-(2-methoxyethoxymethoxy)oxan-2-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 833460-35-8
• 化学式: C₂₇H₃₉N₃O₆Si
• 分子量: 529.709
• InChiKey: BHKFIELIGNFPPX-QYOOZWMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-α-D-ribo-hexopyranoside 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以70%的产率得到3-azido-6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-altronolactone
  参考文献：
  名称：

  Glycal-mediated syntheses of enantiomerically pure 3-azido-2,3-dideoxy-hexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones

  摘要：

  Methodology for the conversion of two commercially available glycals, D-galactal and D-glucal, into 3-azido-2,3-dideoxyhexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones is reported. Using this strategy, templates suitable in combinatorial chemistry for the construction of a number of interesting biologically active molecules have been prepared. Key features of this strategy include the development of an efficient and original reaction sequence for the differential protection of the oxygen functionalities, the regio- and stereoselective introduction of the azido group, and the chemoselective oxidation of the acetal group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.024
• 作为产物：
  描述：

  methyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-mesyl-4-O-(2-methoxyethoxymethyl)-D-arabino-hexopyranoside 在 sodium azide 、 四丁基氯化铵 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以65%的产率得到methyl 3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Glycal-mediated syntheses of enantiomerically pure 3-azido-2,3-dideoxy-hexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones

  摘要：

  Methodology for the conversion of two commercially available glycals, D-galactal and D-glucal, into 3-azido-2,3-dideoxyhexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones is reported. Using this strategy, templates suitable in combinatorial chemistry for the construction of a number of interesting biologically active molecules have been prepared. Key features of this strategy include the development of an efficient and original reaction sequence for the differential protection of the oxygen functionalities, the regio- and stereoselective introduction of the azido group, and the chemoselective oxidation of the acetal group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.024