N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine | 166758-14-1

• 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: N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine
• 英文别名: 2'-deoxy-N⁴-benzoyl-3'-O-t-butyldiphenylsilyl-5-methylcytidine；N-[1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]benzamide
• CAS: 166758-14-1
• 化学式: C₃₃H₃₇N₃O₅Si
• 分子量: 583.759
• InChiKey: VRRYVEIHGLIXIK-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine 在 三苯基膦 、 甲基肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 5'-O-Amino-N⁴-benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 咪唑 、 TMSTf 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037

文献信息

• Synthesis and hybridization properties of an oligonucleotide analog containing a glucose-derived conformation-restricted ribose moiety and 2′, 5′ formacetal linkages
  作者：Ruiming Zou、Mark D Matteucci

  DOI：10.1016/0040-4039(95)02396-8

  日期：1996.2

  A pyrimidine trinucleoside containing a conformationally restricted ribose moiety and two 2′, 5′ formacetal internucleoside linkages was synthesized. The bicyclic ribose moiety was identified by molecular modeling as a candidate to preorder a nucleoside to resemble the bound duplex conformation. The thymine nucleoside analog was simply synthesized from glucose. The trimer was incorporated at the 3′

  合成了具有构象受限的核糖部分和两个2'，5'形成缩醛核苷间键的嘧啶三核苷。通过分子建模将双环核糖部分鉴定为预备核苷类似于结合的双链体构象的候选物。胸腺嘧啶核苷类似物简单地由葡萄糖合成。将三聚体并入较大的未修饰的ON的3'端。发现该嵌合ON类似物对互补RNA的杂交亲和力相对于非构象限制的对照稍差。
• [EN] CONVERGENT LIQUID PHASE SYNTHESES OF OLIGONUCLEOTIDES<br/>[FR] SYNTHÈSES EN PHASE LIQUIDE CONVERGENTE D'OLIGONUCLÉOTIDES
  申请人：BIOGEN MA INC

  公开号：WO2020227618A3

  公开（公告）日：2021-01-14
• Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides
  作者：Michel Perbost、Tomonori Hoshiko、Francois Morvan、Eric Swayze、Richard H. Griffey、Yogesh S. Sanghvi

  DOI：10.1021/jo00121a037

  日期：1995.8

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.