methyl (3a'R,5'R,6'S,6a'S)-6'-(benzyloxy)-5'-((benzyloxy)methyl)tetrahydro-3'H-spiro[cyclopropane-1,2'-furo[3,2-b]furan]-2-carboxylate | 1451180-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3a'R,5'R,6'S,6a'S)-6'-(benzyloxy)-5'-((benzyloxy)methyl)tetrahydro-3'H-spiro[cyclopropane-1,2'-furo[3,2-b]furan]-2-carboxylate
• CAS: 1451180-67-8
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: LEYDAZDDLNBOCS-ITWZLOJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (3a'R,5'R,6'S,6a'S)-6'-(benzyloxy)-5'-((benzyloxy)methyl)tetrahydro-3'H-spiro[cyclopropane-1,2'-furo[3,2-b]furan]-2-carboxylate 在 N-碘代丁二酰亚胺 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 C₂₅H₂₈O₇
  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：

  3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-1,4-lactone 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 methyl (3a'R,5'R,6'S,6a'S)-6'-(benzyloxy)-5'-((benzyloxy)methyl)tetrahydro-3'H-spiro[cyclopropane-1,2'-furo[3,2-b]furan]-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

文献信息

• Stereoselective synthesis of 1,6-dioxaspirolactones from spiro-cyclopropanecarboxylated sugars: total synthesis of dihydro-pyrenolide D
  作者：Bandi Ramakrishna、Perali Ramu Sridhar

  DOI：10.1039/c4ra16753h

  日期：——

  efficient method for the stereoselective construction of 1,6-dioxaspiro[4.n]decan-2-one systems (n = 4, 5) from sugar derived spirocyclopropane carboxylic acids involving a one-pot ring-opening and cyclization reaction is revealed. The generality of the methodology and its application in the total synthesis of dihydro-pyrenolide D and 4-epi-dihydro-pyrenolide D are reported.

  1,6-dioxaspiro立体选择性构建的有效方法[4.。揭示了由糖衍生的螺环丙烷羧酸制得的n ] decan-2-one系统（n = 4、5），涉及一锅开环和环化反应。报道了该方法的一般性及其在二氢-吡咯内酯D和4-表-二氢-吡咯内酯D的全合成中的应用。