1-[(2R,4S,5R)-5-[(1R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]but-3-enyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 189307-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[(2R,4S,5R)-5-[(1R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]but-3-enyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 189307-27-5
• 化学式: C₄₀H₅₀N₂O₇Si
• 分子量: 698.932
• InChiKey: ILMMMZFLIWMKRH-IYKITFJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[(1R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]but-3-enyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 sodium perborate 、 dimethyl sulfide borane 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 5'(R)-C-acetoxypropyl-5'-O-(4,4-dimethoxytrityl)thymidine
  参考文献：
  名称：

  5'- C-羟基烷基胸苷的合成及其掺入寡脱氧核苷酸

  摘要：

  5'- Ç羟基甲基，5'- Ç羟乙基，和5'- Ç -hydroxypropylthymidine衍生物通过四个合成路线，其构成在胸苷的C5'引入不同长度的羟烷基的方法制备。将5'- C-羟甲基-胸苷和5'- C-羟丙基胸苷转化为相应的亚磷酰胺，并掺入寡脱氧核苷酸中。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)00386-9
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 吡啶 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 146.25h， 生成 1-[(2R,4S,5R)-5-[(1R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]but-3-enyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 5′-C-Branched Thymidines and Conversion to Phosphoramidites

  摘要：

  Thymidine was converted to its 5'-epoxy derivative, which was reacted with nucleophiles to give 5'-C-aminomethyl-, 5'-C-bromomethyl-, 5'-C-cyanomethyl, and 5'-C-methoxymethylthymidine derivatives with defined stereochemistry. 5'-C-ally-, 5'-C-hydroxymethyl-, 5'-C-hydroxypropyl-, and 5'-C-(imidazole-4-acetamido)metbylthymidine derivatives were also prepared. The 5'-C-branched thymidines were converted to the corresponding phosphoramidites.

  DOI：

  10.1080/07328319808004219

文献信息

• Synthesis of 5′-C-Hydroxyalkylthymidines and Their Incorporation into Oligodeoxynucleotides
  作者：Guangyi Wang、Patrick J Middleton、Yi-Zhong An

  DOI：10.1016/s0040-4039(97)00386-9

  日期：1997.4

  5′-C-Hydroxymethyl-, 5′-C-hydroxyethyl, and 5′-C-hydroxypropylthymidine derivatives were prepared through four synthetic routes, which constitute an approach to introduce hydroxyalkyl of different lengths at C5′ of thymidine. 5′-C-hydroxymethyl- and 5′-C-hydroxypropylthymidines were converted to the corresponding phosphoramidites and incorporated into oligodeoxynucleotides. © 1997 Elsevier Science

  5'- Ç羟基甲基，5'- Ç羟乙基，和5'- Ç -hydroxypropylthymidine衍生物通过四个合成路线，其构成在胸苷的C5'引入不同长度的羟烷基的方法制备。将5'- C-羟甲基-胸苷和5'- C-羟丙基胸苷转化为相应的亚磷酰胺，并掺入寡脱氧核苷酸中。©1997爱思唯尔科学有限公司。
• 5′-C-branched thymidines: Synthesis, stereochemistry, and incorporation into oligodeoxynucleotides
  作者：Guangyi Wang、Patrick J. Middleton

  DOI：10.1016/0040-4039(96)00418-2

  日期：1996.4

  Thymidine was converted to its 5′(S)-epoxy derivative, which reacted with nucleophiles to give 5′(S)-C-aminomethyl-, 5′(S)-C-azidomethyl-, 5′(S)-C-cyanomethyl-, and 5′(S)-C-methoxymethyl-thymidine with defined stereochemistry. 5′-C-Allyl- and 5′-C-nitromethylthymidines were prepared from an aldehyde derivative. Stereochemistry of 5′-C-branched thymidines was assigned with the help of NOE experiments

  胸苷转化为其5'（小号） -环氧衍生物，其与亲核试剂反应，得到5'（小号） - Ç氨基甲基，5'（小号） - Ç -azidomethyl-，5'（小号） - Ç -氰基甲基，和5'（小号） - c ^甲氧基甲基-胸苷与定义的立体化学。由醛衍生物制备5'- C-烯丙基-和5'- C-硝基甲基胸苷。在NOE实验的帮助下确定了5'- C-支化胸苷的立体化学。将四个5'- C-支化的胸苷掺入寡脱氧核苷酸中。
• Synthesis of 5′-<i>C</i>-Branched Thymidines and Conversion to Phosphoramidites
  作者：Guangyi Wang、Patrick J. Middleton

  DOI：10.1080/07328319808004219

  日期：1998.6

  Thymidine was converted to its 5'-epoxy derivative, which was reacted with nucleophiles to give 5'-C-aminomethyl-, 5'-C-bromomethyl-, 5'-C-cyanomethyl, and 5'-C-methoxymethylthymidine derivatives with defined stereochemistry. 5'-C-ally-, 5'-C-hydroxymethyl-, 5'-C-hydroxypropyl-, and 5'-C-(imidazole-4-acetamido)metbylthymidine derivatives were also prepared. The 5'-C-branched thymidines were converted to the corresponding phosphoramidites.