(+)-3-benzyl-4-hydroxy-hexahydrocyclopenta[d]oxazol-2-one | 611183-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (+)-3-benzyl-4-hydroxy-hexahydrocyclopenta[d]oxazol-2-one
• 英文别名: (3aS,4R,6aR)-3-benzyl-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-2-one
• CAS: 611183-00-7
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: RJRFBYZDTYXYGR-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-3-benzyl-4-hydroxy-hexahydrocyclopenta[d]oxazol-2-one 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-aminocyclopentane-1,3-diol
  参考文献：
  名称：

  Synthesis of a Cyclopentane Amide DNA Analogue and Its Base Pairing Properties

  摘要：

  cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodcoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4degreesC/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible.

  DOI：

  10.1081/ncn-120022837
• 作为产物：
  描述：

  异氰酸苄酯 在 吡啶 、 porcine liver esterase 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (+)-3-benzyl-4-hydroxy-hexahydrocyclopenta[d]oxazol-2-one
  参考文献：
  名称：

  Synthesis of a Cyclopentane Amide DNA Analogue and Its Base Pairing Properties

  摘要：

  cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodcoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4degreesC/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible.

  DOI：

  10.1081/ncn-120022837

文献信息

• Synthesis of Cyclopentane Amide DNA (cpa-DNA) and Its Pairing Properties
  作者：Dae-Ro Ahn、Markus Mosimann、Christian J. Leumann

  DOI：10.1021/jo034143q

  日期：2003.10.1

  We recently reported on the synthesis and pairing properties of the DNA analogue bicyclo[3.2.1]-amide DNA (bca-DNA). In this analogue the nucleobases are attached via a linear, 4-bond amide-linker to a structurally preorganized sugar-phosphate backbone unit. To define the importance of the degree of structural rigidity of the bca-backbone unit on the pairing properties, we designed the structurally simpler cyclopentane amide DNA (cpa-DNA), in which the bicyclo[3.2.1]-scaffold was reduced to a cyclopentane unit while the base-linker was left unchanged. Here we present a synthetic route to the enantiomerically pure cpa-DNA monomers and the corresponding phosphoramidites containing the bases A and T, starting from a known, achiral precursor in 9 and 12 steps, respectively. Fully modified oligodeoxynucleotides were synthesized by standard solid-phase oligonucleotide chemistry, and their base-pairing properties with complementary oligonucleotides of the DNA-, RNA-, bca-DNA-, and cpa-DNA-backbones were assessed by UV melting curves and CD-spectroscopic methods. We found that cpa-oligoadenylates form duplexes with complementary DNA that are less stable by -2.7 degreesC/mod. compared to DNA. The corresponding cpa-oligothymidylates do not participate in complementary base-pairing with any of the investigated backbone systems except with its own (homo-duplex). As its congener bca-DNA, cpa-DNA seems to prefer left-handed helical duplex structures with DNA or with itself as indicated by the CD spectra.