3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid methyl ester | 188198-21-2

• 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: 3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid methyl ester
• CAS: 188198-21-2
• 化学式: C₃₇H₄₄N₂O₇Si
• 分子量: 656.851
• InChiKey: BVJIIIVUWGXGEX-XKKJXBDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid methyl ester 在 lithium hydroxide 、 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 生成 3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2
• 作为产物：
  描述：

  1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2