5-Deoxy-2,3-O-isopropylidenecarba-α-D-lyxo-hexofuranose | 165874-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Deoxy-2,3-O-isopropylidenecarba-α-D-lyxo-hexofuranose
• 英文别名: (3aR,4S,6S,6aS)-6-(2-hydroxyethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 165874-87-3
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: KNYQEMAYJZEYLX-XSPKLOCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Deoxy-2,3-O-isopropylidenecarba-α-D-lyxo-hexofuranose 在 溴 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 6-Bromo-5,6-dideoxy-2,3-isopropylidenecarba-α-D-lyxo-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：

  Benzoic acid (3aR,6R,6aS)-6-methoxycarbonylmethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以86%的产率得到5-Deoxy-2,3-O-isopropylidenecarba-α-D-lyxo-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