rac-1,2-Anhydro-5-deoxycarba-α-xylo-hexofuranurono-6,3-lactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: rac-1,2-Anhydro-5-deoxycarba-α-xylo-hexofuranurono-6,3-lactone
• 英文别名: (1aRS,1bRS,4aSR,5aRS)-hexahydro-3H-oxireno[4,5]cyclopenta[1,2-b]furan-3-one；(1R,2R,4R,6S)-3,9-dioxatricyclo[4.3.0.02,4]nonan-8-one
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: SQHCOEHIVQVUBS-ZXMNWKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-1,2-Anhydro-5-deoxycarba-α-xylo-hexofuranurono-6,3-lactone 在 高氯酸 作用下， 反应 12.0h， 以84%的产率得到rac-5-Deoxycarba-β-xylo-hexofuranurono-6,3-lactone
  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：

  cis-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 在 间氯过氧苯甲酸 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 rac-1,2-Anhydro-5-deoxycarba-α-xylo-hexofuranurono-6,3-lactone
  参考文献：
  名称：

  [EN] NITROOXY CYCLOALKANE DERIVATIVES
  [FR] DÉRIVÉS DE NITROOXY CYCLOALCANE

  摘要：

  一种具有以下结构的化合物，其中Y选择自- C（O）OR2，- C（O）NHR8，- C（CH2）1-2OR3，OH等组成的群体，或其药用盐，并使用这些化合物治疗高血压的方法。

  公开号：

  WO2010062415A1

文献信息

• Synthesis of Carbasugars from Aldonolactones: Ritter-Type Epoxide Opening in the Synthesis of Polyhydroxylated Aminocyclopentanes
  作者：Steen K. Johansen、Hanne T. Kornø、Inge Lundt

  DOI：10.1055/s-1999-3690

  日期：1999.1

  Using the cis-fused cyclopentane-1,4-lactone, (1R,5S,7R,8R)-7,8-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one (1), as starting material, 5-deoxycarba-β-l-xylo-hexofuranose (6) together with α- (12) and β-1-amino-1,5-dideoxycarba-l-xylo-hexofuranose (16) have been prepared using a number of stereoselective transformations. The key step was the regioselective opening of the epoxide (1R,5S,7R,8R)-7,8-epoxy-2-oxabicyclo-[3.3.0]oct-3-one (4) with different nucleophiles.

  以顺式融合的环戊烷-1,4-内酯 (1R,5S,7R,8R)-7,8-二羟基-2-氧杂双环[3.3.以辛-3-酮 (1) 为起始原料，通过一系列立体选择性转化，制备出了 5-脱氧卡巴-δ-l-氧基六呋喃糖 (6) 以及δ-(12) 和 δ-1-氨基-1,5-二脱氧卡巴-l-氧基六呋喃糖 (16)。关键步骤是用不同的亲核剂打开环氧化物 (1R,5S,7R,8R)-7,8-环氧-2-氧杂二环-[3.3.0]辛-3-酮 (4)。