3-O-acetyl-5-(E)-eno-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose | 95881-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-5-(E)-eno-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
• 英文别名: 3-O-acetyl-1,2-O-isopropylidene-4-(trans-3-oxobutenyl)-α-D-threofuranose；[(3aR,5R,6S,6aR)-2,2-dimethyl-5-[(E)-3-oxobut-1-enyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 95881-36-0
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: CXOCZQOAZPCNBZ-NBUZQSQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-5-(E)-eno-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose 在 吡啶 作用下， 以 四氯化碳 为溶剂， 反应 960.0h， 生成
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006
• 作为产物：
  描述：

  乙酸酐 、 1-三苯基膦-2-丙酮 、 1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium periodate 、 吡啶 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以52%的产率得到3-O-acetyl-5-(E)-eno-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006

文献信息

• Loss or transfer of an acetyl group during Knoevenagel reactions of aldehydo sugars with acetylacetone
  作者：F.J.Lopez Aparicio、F.Zorrilla Benitez、P.Garcia Mendoza、F.Santoyo Gonzalez

  DOI：10.1016/s0008-6215(00)90781-x

  日期：1985.1