[(2S,3R,4S)-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 | 848842-36-4

• 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: [(2S,3R,4S)-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
• CAS: 848842-36-4
• 化学式: C₂₉H₃₄O₉
• 分子量: 526.584
• InChiKey: KIGHHUSTJJFOHO-RLRFXSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S)-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 、 三甲基硅烷化重氮甲烷 在 正丁基锂 、 三甲基氯硅烷 、 二异丙胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 甲醇 、 苯 为溶剂， 以22%的产率得到(3aR,4S,6S,6aS)-6-Benzyloxy-4-((5R,6S)-5-benzyloxy-6-methoxy-5,6-dihydro-2H-pyran-3-ylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
  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：

  methyl 2-O-benzyl-3,4-O-isopropylidene-β-L-arabinopyranoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 水 、 对甲苯磺酸 、 溶剂黄146 、 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 1.0h， 生成 [(2S,3R,4S)-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

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.