methyl (R)-2,3-dideoxy-2,3-<(ethoxycarbonyl)methylene>-α-D-mannopyranoside | 133969-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (R)-2,3-dideoxy-2,3-<(ethoxycarbonyl)methylene>-α-D-mannopyranoside
• CAS: 133969-98-9
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: CXYZUDCHFGIDDY-GLIXCWQDSA-N

反应信息

• 作为反应物：
  描述：

  methyl (R)-2,3-dideoxy-2,3-<(ethoxycarbonyl)methylene>-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 吡啶 为溶剂， 反应 8.0h， 生成 methyl (R)-1,4,6-tri-O-acetyl-2,3-dideoxy-2,3-<(ethoxycarbonyl)methylene>-D-mannopyranose
  参考文献：
  名称：

  Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals

  摘要：

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.

  DOI：

  10.1021/jo00012a009
• 作为产物：
  描述：

  (1S,1aR,2S,3aR,6R,7aS,7bS)-2-Methoxy-6-phenyl-hexahydro-3,5,7-trioxa-cyclopropa[a]naphthalene-1-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 17.0h， 生成 methyl (R)-2,3-dideoxy-2,3-<(ethoxycarbonyl)methylene>-α-D-mannopyranoside
  参考文献：
  名称：

  Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals

  摘要：

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.

  DOI：

  10.1021/jo00012a009