5-Deoxycarba-α-D-ribo-hexofuranose | 145840-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Deoxycarba-α-D-ribo-hexofuranose
• 英文别名: (+)-(1S,2S,3R,4S)-4-(2'-Hydroxyethyl)cyclopentane-1,2,3-triol；(1S,2S,3R,4S)-4-(2-hydroxyethyl)cyclopentane-1,2,3-triol
• CAS: 145840-34-2
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: VEEPYKLZGBGFKI-YTLHQDLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-Deoxycarba-α-D-ribo-hexofuranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,2,3,6-Tetra-O-acetyl-5-deoxycarba-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Synthesis of All Stereoisomeric Carbapentofuranoses

  摘要：

  All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer-Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyre, and alpha-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3-position was found. If an epoxy acetate with both functions on the same side of the ring was used, the epoxide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.

  DOI：

  10.1021/jo00121a046
• 作为产物：
  描述：

  (Z)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acrylic acid ethyl ester 在 palladium on activated charcoal 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 142.0h， 生成 5-Deoxycarba-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Radical cyclisation reactions leading to polyhydroxylated cyclopentane derivatives: synthesis of (1R,2R,3S,4R)- and (1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triol

  摘要：

  The tetraol (-)-1 has been prepared from a derivative of (D)-allose 3. The stereoselective carbocyclization reaction (8 double line arrow pointing right 11) formed the key step in this sequence. The enantiomeric cyclopentane derivative(+)-1 was also prepared from compound 3.In this synthesis the cyclization of compound 18 to provide the carbocycle 19 features as the critical carbon-carbon bond forming reaction.

  DOI：

  10.1039/p19920002625