1,3,6-tri-O-benzyl-D-mannitol | 1160933-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,6-tri-O-benzyl-D-mannitol
• 英文别名: (2R,3R,4R,5R)-1,4,6-tris(phenylmethoxy)hexane-2,3,5-triol
• CAS: 1160933-52-7
• 化学式: C₂₇H₃₂O₆
• 分子量: 452.547
• InChiKey: IVMIFASWEKAYOA-FPCALVHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl 2,6-di-O-benzyl-α-D-glucopyranoside 、 溴甲苯 在 二正丁基氧化锡 、 四丁基溴化铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.0h， 以49%的产率得到1,3,6-tri-O-benzyl-D-mannitol
  参考文献：
  名称：

  Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals

  摘要：

  A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse Structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially at the corresponding stannylene acetals (only similar to 1.0 mol equiv of Bu2SnO was employed). It was also demonstrated that one might exert control over the number of protected groups, by means of appropriate tuning of reaction conditions. The feasibility of a substoichiometric (tin source) catalytic protocol was demonstrated as well. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.114

文献信息

• Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals
  作者：Alessandro B.C. Simas、Angelo A.T. da Silva、Tarcizio J. dos Santos Filho、Pedro T.W. Barroso

  DOI：10.1016/j.tetlet.2009.03.114

  日期：2009.6

  A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse Structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially at the corresponding stannylene acetals (only similar to 1.0 mol equiv of Bu2SnO was employed). It was also demonstrated that one might exert control over the number of protected groups, by means of appropriate tuning of reaction conditions. The feasibility of a substoichiometric (tin source) catalytic protocol was demonstrated as well. (C) 2009 Elsevier Ltd. All rights reserved.