methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside | 848842-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside
• 英文别名: (3R,4R,5S,6R)-6-methoxy-5-phenylmethoxy-4-prop-2-enoxyoxan-3-ol
• CAS: 848842-27-3
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: QJJGIKNAUFGVPH-LVQVYYBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 [(2R,3S,4R)-2-methoxy-5-methylidene-3-phenylmethoxyoxan-4-yl] (3aS,4S,6S,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylate
  参考文献：
  名称：

  Synthesis of novel types of divalent saccharide structures by a ketene acetal Claisen rearrangement

  摘要：

  A simple allyl uronate was rearranged to give the branched product, which in turn could be transformed into a spiroannellated bicyclic compound. More complex allyl uronates of D-and L-arabinose were rearranged to give novel methylene-bridged dimeric saccharide structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.001
• 作为产物：
  描述：

  3-溴丙烯 、 methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside 在 水 、 溶剂黄146 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside
  参考文献：
  名称：

  Synthesis of novel types of divalent saccharide structures by a ketene acetal Claisen rearrangement

  摘要：

  A simple allyl uronate was rearranged to give the branched product, which in turn could be transformed into a spiroannellated bicyclic compound. More complex allyl uronates of D-and L-arabinose were rearranged to give novel methylene-bridged dimeric saccharide structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.001

文献信息

• Synthesis of novel types of divalent saccharide structures by a ketene acetal Claisen rearrangement
  作者：Barbara Werschkun、Joachim Thiem

  DOI：10.1016/j.tetasy.2004.12.001

  日期：2005.1

  A simple allyl uronate was rearranged to give the branched product, which in turn could be transformed into a spiroannellated bicyclic compound. More complex allyl uronates of D-and L-arabinose were rearranged to give novel methylene-bridged dimeric saccharide structures. (C) 2004 Elsevier Ltd. All rights reserved.