ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate | 136839-01-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate
• 英文别名: ethyl 3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate
• CAS: 136839-01-5
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: HJNHADRSSAHDCO-APHKKCJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate 在 吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  合成手性，多官能团的环戊烷环的新合成途径

  摘要：

  氢化三丁基锡介导的糖衍生物4–6的自由基环化使环状呋喃糖酶9–11具有较高的收率和较高的非对映选择性。该方案是用于制备复杂的环戊烷分子的新的合成途径。

  DOI：

  10.1016/s0040-4039(00)79149-0
• 作为产物：
  描述：

  (Z)-ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-eno-1,4-furanuronate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate
  参考文献：
  名称：

  Total synthesis of griseolic acid derivatives from D-glucose

  摘要：

  Griseolic acid, 1, is a potent nonselective cyclic nucleotide-phosphodiesterase inhibitor isolated from Streptomyces Griseoaurantiacus. Recently, preparation of several griseolic acid derivatives, including 3, has been reported. We have completed the chiral total synthesis of several griseolic acid derivatives. Here, we report on total syntheses of two cis-fused 4',5'-dihydro-7'-deoxy griseolic acid derivatives, 4 and 5, from D-glucose.

  DOI：

  10.1021/jo00024a022

文献信息

• Studies Directed toward the Development of Amide-Linked RNA Mimics: Synthesis of the Monomeric Building Blocks
  作者：Tushar Kanti Chakraborty、Praveen Kumar Gajula、Dipankar Koley

  DOI：10.1021/jo801156a

  日期：2008.9.1

  A general approach toward the synthesis of all four monomeric building blocks of the ribonucleoside amino acids 3'-amino-5'-carboxymethyl-3',5'-dideoxy nucleosides in their protected forms is described that will facilitate the development of amide-linked RNA mimics.

  描述了一种以其保护形式合成核糖核苷氨基酸3'-氨基-5'-羧甲基-3'，5'-二脱氧核苷的所有四个单体结构单元的通用方法，该方法将促进酰胺连接的发展RNA模拟物。
• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.