Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-phosphonooxy-tetrahydro-furan-3-yl ester | 162308-07-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-phosphonooxy-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)-4-phosphonooxyoxolan-3-yl] hydrogen phosphate
• CAS: 162308-07-8
• 化学式: C₁₈H₂₄N₄O₁₇P₂
• 分子量: 630.353
• InChiKey: XRSMAWMALLFSQQ-NCOIDOBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  301
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-phosphonooxy-tetrahydro-furan-3-yl ester 在 ammonium acetate 作用下， 以 水 为溶剂， 生成 尿苷酰基-(3',5')-尿苷
  参考文献：
  名称：

  New Strategies for the Chemical Synthesis of Biologically Important Nucleic Acid Derivatives

  摘要：

  This paper describes general methods for the synthesis of N-phosphorylated ribonucleosides and oligonucleotides containing a 2'-O-phosphorylated or 2'-O-thiophosphorylated ribonucleoside. The NMR-based conformational analysis and computational molecular dynamics simulation of the 2'-O-phosphorylated ribonucleoside residue in such modified oligonucleotides suggested that the ribose residue existed preferentially in a C2'-endo conformation, it was also found that simple heating of 2'-O-phosphorylated oligonucleotides resulted in rapid dethiophosphorylation.

  DOI：

  10.1080/07328319808004744
• 作为产物：
  描述：

  生成 Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-phosphonooxy-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  New Strategies for the Chemical Synthesis of Biologically Important Nucleic Acid Derivatives

  摘要：

  This paper describes general methods for the synthesis of N-phosphorylated ribonucleosides and oligonucleotides containing a 2'-O-phosphorylated or 2'-O-thiophosphorylated ribonucleoside. The NMR-based conformational analysis and computational molecular dynamics simulation of the 2'-O-phosphorylated ribonucleoside residue in such modified oligonucleotides suggested that the ribose residue existed preferentially in a C2'-endo conformation, it was also found that simple heating of 2'-O-phosphorylated oligonucleotides resulted in rapid dethiophosphorylation.

  DOI：

  10.1080/07328319808004744

文献信息

• Studies on Steric and Electronic Control of 2‘−3‘ Phosphoryl Migration in 2‘-Phosphorylated Uridine Derivatives and Its Application to the Synthesis of 2‘-Phosphorylated Oligouridylates
  作者：Mitsuo Sekine、Hiroyuki Tsuruoka、Shin Iimura、Hiroshi Kusuoku、Takeshi Wada、Kiyotaka Furusawa

  DOI：10.1021/jo952073k

  日期：1996.1.1

  phosphitylation with bis(2-cyano-1,1-dimethylethoxy)(diethylamino)phosphine followed by sulfurization. Treatment of the 2'-thiophosphorylated product 15 with (HF)(x)().Py in THF gave exclusively the 3',5'-unprotected uridine derivative 16a. Compound 16a was converted to the phosphoramidite unit 22 via a two-step reaction. This building block was used for the solution phase synthesis of U(2'-p)pU (29)

  对于通过使用新的亚磷酰胺结构单元合成2'-磷酸化的低聚吡啶二酸酯，已经研究了几种掩蔽的磷酰基作为2'-磷酸酯前体，当3'羟基保护基必须是3'羟基时，不应将其迁移到3'位置。去除亚磷酰胺残基，将其引入3'-位。结果，发现双（2-氰基-1,1-二甲基乙氧基）硫代磷酰基（BCMETP）是最合适的2'-磷酸盐前体。该硫代磷酰基可通过与双（2-氰基-1，1-二甲基乙氧基）（二乙氨基）膦进行磷酸化，然后硫化而引入3'，5'-甲硅烷基化尿苷衍生物7的2'-羟基。用（HF）（x）（）。Py在THF中处理2'-硫代磷酸化产物15，仅得到3'，5' -未保护的尿苷衍生物16a。化合物16a通过两步反应被转化为亚磷酰胺单元22。该构件用于U（2'-p）pU（29）和U（2'-ps）pU（30）的溶液相合成。通过在N，O-双（三甲基甲硅烷基）乙酰胺（BSA）存在下用DBU处理，从完全保护的衍生物25中有效除去2-