5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine | 171176-08-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine
• 英文别名: TBDPS(-3)[H2N(-5)]Ribf2Me(b)-thymin-1-yl；1-[(2R,3R,4R,5R)-5-(aminooxymethyl)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 171176-08-2
• 化学式: C₂₇H₃₅N₃O₆Si
• 分子量: 525.677
• InChiKey: RWYNYSCOXDSCDL-VWBWNGLSSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine 在 sodium cyanoborohydride 、 溶剂黄146 、 三氯乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.67h， 生成
  参考文献：
  名称：

  Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs

  摘要：

  The synthesis of a series of methylene(methylimino) (MMI) linked oligodeoxyribonucleotide dimers modified at the 2'-position with fluoro and/or methoxy groups and their incorporation into different sequences has been accomplished. From these dimers, his 2'-OMe MMI dimer was selected for further studies based on its synthetic accessibility and the increased thermodynamic stability conferred upon oligonucleotides incorporating this modification.

  DOI：

  10.1081/ncn-120028337
• 作为产物：
  描述：

  3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5'-O-phthalimido-5-methyluridine 在 甲基肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine
  参考文献：
  名称：

  Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs

  摘要：

  The synthesis of a series of methylene(methylimino) (MMI) linked oligodeoxyribonucleotide dimers modified at the 2'-position with fluoro and/or methoxy groups and their incorporation into different sequences has been accomplished. From these dimers, his 2'-OMe MMI dimer was selected for further studies based on its synthetic accessibility and the increased thermodynamic stability conferred upon oligonucleotides incorporating this modification.

  DOI：

  10.1081/ncn-120028337

文献信息

• An Efficient Multigram Synthesis of Monomers for the Preparation of Novel Oligonucleotides Containing Isosteric Non-Phosphorous Backbones
  作者：Stuart Dimock、Balkrishen Bhat、Didier Peoc'h、Yogesh S. Sanghvi、Eric E. Swayze

  DOI：10.1080/07328319708006242

  日期：1997.7

  The facile preparation of two novel classes of nucleoside analogs for the inclusion as dimeric non-phosphorous containing subunits in chimeric backbones has been accomplished. The concise preparation of 3'-formylnucleosides and 5'-O-(N-methylhydroxylamino)-nucleosides is reported.
• Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs
  作者：Didier Peoc'h、Eric E. Swayze、Balkrishen Bhat、Yogesh S. Sanghvi

  DOI：10.1081/ncn-120028337

  日期：2004.1.1

  The synthesis of a series of methylene(methylimino) (MMI) linked oligodeoxyribonucleotide dimers modified at the 2'-position with fluoro and/or methoxy groups and their incorporation into different sequences has been accomplished. From these dimers, his 2'-OMe MMI dimer was selected for further studies based on its synthetic accessibility and the increased thermodynamic stability conferred upon oligonucleotides incorporating this modification.