4-amino-1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-[(methylideneamino)oxymethyl]oxolan-2-yl]-5-methylpyrimidin-2-one | 183737-36-2

• 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: 4-amino-1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-[(methylideneamino)oxymethyl]oxolan-2-yl]-5-methylpyrimidin-2-one
• CAS: 183737-36-2
• 化学式: C₂₈H₃₆N₄O₅Si
• 分子量: 536.703
• InChiKey: KAYCFYHMGPOHFF-PMHJDTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-[(methylideneamino)oxymethyl]oxolan-2-yl]-5-methylpyrimidin-2-one 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 4-Amino-1-{(2R,3R,4R,5R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-5-[(N-methyl-aminooxy)-methyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one
  参考文献：
  名称：

  An Efficient Multigram Synthesis of Monomers for the Preparation of Novel Oligonucleotides Containing Isosteric Non-Phosphorous Backbones

  摘要：

  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.

  DOI：

  10.1080/07328319708006242
• 作为产物：
  描述：

  5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine 在 1H-1,2,3-三氮唑 、 氨 、 三氯氧磷 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 4-amino-1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-[(methylideneamino)oxymethyl]oxolan-2-yl]-5-methylpyrimidin-2-one
  参考文献：
  名称：

  An Efficient Multigram Synthesis of Monomers for the Preparation of Novel Oligonucleotides Containing Isosteric Non-Phosphorous Backbones

  摘要：

  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.

  DOI：

  10.1080/07328319708006242

文献信息

• A mild and highly selective N-benzoylation of cytosine and adenine bases in nucleosides with N-benzoyltetrazole
  作者：Balkrishen Bhat、Yogesh S. Sanghvi

  DOI：10.1016/s0040-4039(97)10423-3

  日期：1997.12

  N-Benzoyltetrazole has been developed as a mild and selective reagent for monobenzoylation of the exocyclic amino group in nucleic acid bases. its usefulness is demonstrated by protection of adenine and cytosine bases, an important procedure in the nucleic acid chemistry field. (C) 1997 Elsevier Science Ltd.
• 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.