1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-D-arabino-hex-1-enitol | 833460-29-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-D-arabino-hex-1-enitol
• CAS: 833460-29-0
• 化学式: C₂₆H₃₆O₆Si
• 分子量: 472.654
• InChiKey: FUXJXTSNRDTDNQ-SDHSZQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-D-arabino-hex-1-enitol 在 三苯基膦氢溴酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-α-D-arabino-hexopyranoside 、 methyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-β-D-arabino-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
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 咪唑 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(2-methoxyethoxymethyl)-D-arabino-hex-1-enitol
  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