1-O-methanesulfonyl-2-O-methyl-3,4-O-acetyl-6-O-(4-toluoyl)-D-psicofuranose | 783322-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methanesulfonyl-2-O-methyl-3,4-O-acetyl-6-O-(4-toluoyl)-D-psicofuranose
• 英文别名: [(2R,3R,4R)-3,4-diacetyloxy-5-methoxy-5-(methylsulfonyloxymethyl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 783322-62-3
• 化学式: C₂₀H₂₆O₁₁S
• 分子量: 474.486
• InChiKey: QSEOPBSRKONRLN-KYJJNMIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-O-methanesulfonyl-2-O-methyl-3,4-O-acetyl-6-O-(4-toluoyl)-D-psicofuranose 在 吡啶 、 三甲基氯硅烷 、 二异丙基铵盐四氮唑 、 四丁基氟化铵 、 氨 、 氢溴酸 、 sodium hexamethyldisilazane 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 82.57h， 生成 9-{1',3'-O-anhydro-4'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl}-N⁶-(phenoxyacetyl)-adenine
  参考文献：
  名称：

  Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues

  摘要：

  We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia cells. Here we report on the straightforward syntheses of the oxetane-A and oxetane-G nucleosides as well as their incorporations into antisense oligonucleotides (AONs), and compare their structural and antisense properties with those of the T and C modified AONs (including the thermostability and RNase H recruitment capability of the AON/RNA hybrid duplex by Michaelis-Menten kinetic analyses, their resistance in the human serum, as well as in the presence of exo and endonucleases).

  DOI：

  10.1021/ja048417i
• 作为产物：
  描述：

  2-O-methyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-D-psicofuranose 在 吡啶 、 三氟乙酸 作用下， 反应 15.42h， 生成 1-O-methanesulfonyl-2-O-methyl-3,4-O-acetyl-6-O-(4-toluoyl)-D-psicofuranose
  参考文献：
  名称：

  Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues

  摘要：

  We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia cells. Here we report on the straightforward syntheses of the oxetane-A and oxetane-G nucleosides as well as their incorporations into antisense oligonucleotides (AONs), and compare their structural and antisense properties with those of the T and C modified AONs (including the thermostability and RNase H recruitment capability of the AON/RNA hybrid duplex by Michaelis-Menten kinetic analyses, their resistance in the human serum, as well as in the presence of exo and endonucleases).

  DOI：

  10.1021/ja048417i