4,5-O-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal | 519057-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-O-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal
• CAS: 519057-03-5
• 化学式: C₁₅H₂₆O₃S₂
• 分子量: 318.502
• InChiKey: CUFHCHANXYAMMU-OLZOCXBDSA-N

反应信息

• 作为反应物：
  描述：

  4,5-O-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (S)-4-Ethylsulfanyl-5-hydroxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  摘要：

  2,3: 4,5-Di-O-cyclohexylidene-L-arabinose diethyl dithioacetal was treated with sodium methyl-sulfinylmethylide to prepare a novel compound, 4,5-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal. The product undergoes a series of transformations in anhydrous ethanol in the presence of p-toluenesulfonic acid: alcoholysis of the cyclohexylidene protection, elimination of water, migration of the double bond, formation of an acyclic allyl cation, elimination of the ethylthio group, formation of a cyclic allyl cation, migration of the mercapto group from C-1 to C-3, addition of alcohol, and formation of an acetalized lactone. The latter was acetalized to obtain a diastereomeric mixture of 5-O-acetyl-2-deoxy-3-S-ethyl-L-threo- and -erythro-pentono-1,4-lactones.

  DOI：

  10.1023/a:1020883930615
• 作为产物：
  描述：

  2,3:4,5-di-O-cyclohexylidene-L-arabinose diethyl dithioacetal 在 sodium 、 二甲基亚砜 作用下， 反应 0.5h， 以97%的产率得到4,5-O-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal
  参考文献：
  名称：

  摘要：

  2,3: 4,5-Di-O-cyclohexylidene-L-arabinose diethyl dithioacetal was treated with sodium methyl-sulfinylmethylide to prepare a novel compound, 4,5-cyclohexylidene-2-deoxy-L-erythro-pent-1-enose diethyl dithioacetal. The product undergoes a series of transformations in anhydrous ethanol in the presence of p-toluenesulfonic acid: alcoholysis of the cyclohexylidene protection, elimination of water, migration of the double bond, formation of an acyclic allyl cation, elimination of the ethylthio group, formation of a cyclic allyl cation, migration of the mercapto group from C-1 to C-3, addition of alcohol, and formation of an acetalized lactone. The latter was acetalized to obtain a diastereomeric mixture of 5-O-acetyl-2-deoxy-3-S-ethyl-L-threo- and -erythro-pentono-1,4-lactones.

  DOI：

  10.1023/a:1020883930615