2,4-Dideoxy-5,6-O-isopropylidene-D-glucose Diethyl Dithioacetal | 138386-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-Dideoxy-5,6-O-isopropylidene-D-glucose Diethyl Dithioacetal
• 英文别名: (2S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,4-bis(ethylsulfanyl)butan-2-ol
• CAS: 138386-38-6
• 化学式: C₁₃H₂₆O₃S₂
• 分子量: 294.48
• InChiKey: JVBITTCTPVGVCT-QWRGUYRKSA-N

物化性质

• 沸点：
  381.7±32.0 °C(predicted)
• 密度：
  1.082±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,4-Dideoxy-5,6-O-isopropylidene-D-glucose Diethyl Dithioacetal 在 三氟化硼乙醚 、 三苯基膦 、 mercury(II) oxide 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 Methyl α-2,4-Dideoxy-3-(p-nitrobenzoyl)-D-allopyranoside
  参考文献：
  名称：

  Practical synthesis of an enantiomerically pure intermediate of the lactone moiety of mevinic acids

  摘要：

  DOI：

  10.1021/jo00031a056
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 5.5h， 生成 2,4-Dideoxy-5,6-O-isopropylidene-D-glucose Diethyl Dithioacetal
  参考文献：
  名称：

  Practical synthesis of an enantiomerically pure intermediate of the lactone moiety of mevinic acids

  摘要：

  DOI：

  10.1021/jo00031a056

文献信息

• Stereoelectronic effects in the 6-exo free radical cyclization of acyclic sugar derivatives: synthesis of branched chain cyclitols
  作者：Jose Marco-Contelles、Belen Sanchez

  DOI：10.1021/jo00068a025

  日期：1993.7

  The synthesis and free radical carbocyclization (BU3SnH + AIBN) of acyclic sugar derivatives 1-12 is reported. The yields of these 6-exo cyclization processes are good and the diastereomeric excesses are from moderate to excellent. The resulting cyclohexanes are polyoxygenated, enantiomerically pure building blocks for the synthesis of complex branched chain cyclitols. The results obtained in the cyclization of radical precursors 1, 4, 6, and 8 are in sharp contrast with the results observed in the ring closure of compounds 2, 3, 5, and 7. An electron-attracting group (acetate or mesylate), located in a vicinal position to the carbon-centered radical, modifies the conformation of the reacting species in the transition state and thus changes the stereochemical outcome of the cyclization. This allowed us to select the nature of the absolute configuration at the newly formed stereocenter by simply changing the type of the substituents at the vicinal carbon where the radical is generated.