2,6-anhydro-7,8-dideoxy-1,3,4,5-tetra-O-methyl-D-glycero-D-manno-nonitol | 1057653-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-7,8-dideoxy-1,3,4,5-tetra-O-methyl-D-glycero-D-manno-nonitol
• CAS: 1057653-67-4
• 化学式: C₁₃H₂₆O₆
• 分子量: 278.346
• InChiKey: IOJJTCQVNWNVRR-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  N-羟基邻苯二甲酰亚胺 、 2,6-anhydro-7,8-dideoxy-1,3,4,5-tetra-O-methyl-D-glycero-D-manno-nonitol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到2,6-anhydro-7,8-dideoxy-1,3,4,5-tetra-O-methyl-9-O-phthalimido-D-glycero-D-manno-nonitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070
• 作为产物：
  描述：

  2,6-anhydro-7,8,9,10-tetradeoxy-O-methyl-D-glycero-D-manno-dec-9-enitol 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到2,6-anhydro-7,8-dideoxy-1,3,4,5-tetra-O-methyl-D-glycero-D-manno-nonitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070