(3aS,4R,6S,6aR)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol | 129885-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6S,6aR)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
• CAS: 129885-81-0
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: KNYQEMAYJZEYLX-KDXUFGMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,6aR)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 在 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 生成 (3aR,6R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-4-one
  参考文献：
  名称：

  Synthesis of α- and β-D-carbaribofuranose from (+)-norborn-5-en-2-one

  摘要：

  DOI：

  10.1016/0040-4039(90)80170-q
• 作为产物：
  描述：

  methyl 2-[(1R,4R)-4-acetyloxycyclopent-2-en-1-yl]acetate 在 四氧化锇 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 17.5h， 生成 (3aS,4R,6S,6aR)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
  参考文献：
  名称：

  α-和β-D，L-核糖-carbahex-2-ulofuranose的合成

  摘要：

  α-和β-D，L-核糖-氨基-2--2-呋喃呋喃糖均以降冰片烯-2-酮为外消旋形式合成。在合成过程中，硫酰化物与α-烷氧基酮的反应采用了意想不到的立体化学途径。

  DOI：

  10.1016/s0040-4020(01)81872-x

文献信息

• Synthesis of All Stereoisomeric Carbapentofuranoses
  作者：Christoph Marschner、Judith Baumgartner、Herfried Griengl

  DOI：10.1021/jo00121a046

  日期：1995.8

  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.