9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine | 783322-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine
• 英文别名: N-[9-[(1R,3R,4R,5R)-3-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-2,6-dioxabicyclo[3.2.0]heptan-1-yl]purin-6-yl]-2-phenoxyacetamide
• CAS: 783322-66-7
• 化学式: C₄₀H₃₇N₅O₈
• 分子量: 715.762
• InChiKey: ZMVOITWQPQFYRY-FCOKYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到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：

  6-O-(4-toluoyl)-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 在 吡啶 、 盐酸 、 三甲基氯硅烷 、 四丁基氟化铵 、 氨 、 氢溴酸 、 sodium hexamethyldisilazane 、 溶剂黄146 、 六甲基二硅氮烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 97.99h， 生成 9-[1',3'-O-anhydro-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

文献信息

• Facile preparation of the oxetane-nucleosides
  作者：Małgorzata Bogucka、Petr Nauš、Wimal Pathmasiri、Jharna Barman、Jyoti Chattopadhyaya

  DOI：10.1039/b511406c

  日期：——

  Efficient and practical large scale synthesis of suitably protected 1′,2′-oxetane locked purine and pyrimidine nucleosides for incorporation in oligo-DNA or -RNA by solid-phase synthesis is reported. A high regio and stereoselectivity with preferential formation of the β-anomer in the glycosylation reaction, using the Vorbrüggen procedure, was achieved by a convergent synthetic procedure with orthogonal protection strategy using either 1,2-di-O-acetyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-D-psicofuranose or 2-O-acetyl-6-O-benzyl-1,3,4-tri-O-(4-toluoyl)-D-psicofuranose as the glycosyl donor.

  据报道，有效且实用的大规模合成适当保护的 1',2'-氧杂环丁烷锁定的嘌呤和嘧啶核苷，用于通过固相合成掺入寡聚 DNA 或 RNA。使用 Vorbrüggen 程序，通过采用 1,2-二-O-乙酰基-3,4- 的正交保护策略的收敛合成程序，实现了高区域选择性和立体选择性，并在糖基化反应中优先形成 β-端基异构体。 O-异亚丙基-6-O-(4-甲苯酰基)-D-呋喃酮糖或2-O-乙酰基-6-O-苄基-1,3,4-三-O-(4-甲苯酰基)-D-呋喃酮糖糖基供体。
• 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
  作者：Pushpangadan I. Pradeepkumar、Pradeep Cheruku、Oleksandr Plashkevych、Parag Acharya、Suresh Gohil、Jyoti Chattopadhyaya

  DOI：10.1021/ja048417i

  日期：2004.9.1

  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).