methyl (5R,6R,7S)-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-4-oxaspiro[2.4]heptane-2-carboxylate | 1451180-51-0

• 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: methyl (5R,6R,7S)-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-4-oxaspiro[2.4]heptane-2-carboxylate
• CAS: 1451180-51-0
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: YLEDJGRMAFBJAT-YCJKBQJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (5R,6R,7S)-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-4-oxaspiro[2.4]heptane-2-carboxylate 在 N-碘代丁二酰亚胺 、 水 作用下， 以 1,4-二氧六环 为溶剂， 以67%的产率得到C₃₀H₃₂O₇
  参考文献：
  名称：

  Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

  摘要：

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

  DOI：

  10.1021/ol402021e
• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-D-arabino-hex-1-enitol 、 重氮乙酸甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到methyl (5R,6R,7S)-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-4-oxaspiro[2.4]heptane-2-carboxylate
  参考文献：
  名称：

  Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

  摘要：

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

  DOI：

  10.1021/ol402021e