5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine | 154468-74-3

• 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: 5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-3'-C-hydroxymethylthymidine；5'-O-(4,4'-dimethoxytrityl)-3'-hydroxymethylthymidine；1-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-4-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 154468-74-3
• 化学式: C₃₂H₃₄N₂O₈
• 分子量: 574.631
• InChiKey: QERLLGHXKILWGB-QIBDARBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine 在 吡啶 、 咪唑 、 N-甲基吲哚酮 、 cerium(III) chloride 、 四丙基高钌酸铵 、 4 Angstroems MS 、 氢氟酸 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 37.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-C-(2,2-dimethylpropanoyl)thymidine
  参考文献：
  名称：

  C-3‘-Branched Thymidines as Precursors for the Selective Generation of C-3‘-Nucleoside Radicals

  摘要：

  C-3'-nucleoside radicals can be generated via Norrish type I photocleavage of C-3'-acyl nucleoside derivatives. In monomer experiments employing C-3'-acylthymidine derivatives 2 and 3, a 1:1 mixture of isomers of the H-abstraction products was obtained when the photolysis was carried out in the presence of a hydrogen donor. Derivatives 2 were synthesized by an approach which involves the formation of a silyl-protected cyanohydrin, which is subsequently alkylated with organolithium reagents, followed by hydrolysis. Derivatives 3 could be obtained via a multistep synthesis starting from diol 7. Several different methods were attempted to oxidize the unprotected diol to the alpha-hydroxy aldehyde. Finally, a route was chosen which involves a protection-deprotection sequence followed by oxidation of the free primary alcohol. The resulting modified nucleosides should facilitate the study of C-3'-DNA radicals.

  DOI：

  10.1021/jo982022y
• 作为产物：
  描述：

  保护胸苷 在 吡啶 、 四氧化锇 、 重铬酸吡啶 、 3 A molecular sieve 、 四氯化钛 、 N-甲基吗啉氧化物 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine
  参考文献：
  名称：

  Jørgensen, Pia N.; Stein, Paul C.; Wengel, Jesper, Journal of the American Chemical Society, 1994, vol. 116, # 5, p. 2231 - 2232

  摘要：

  DOI：

文献信息

• Sugar modified nucleosides and their use for synthesis of
  申请人：ICN Pharmaceuticals

  公开号：US05712378A1

  公开（公告）日：1998-01-27

  A number of modified nucleosides are disclosed composed of modified sugar moieties which contain substituents at C1 and C4 positions, or branched substituents at C3 and C5 positions of deoxyribose or ribose. Each nucleoside is converted to or properly protected and then converted to the corresponding phosphoramidites. These phosphoramidites are used to assemble oligonucleotides in which there is at least one of the forenoted nucleosides. These sugar modified oligonucleotides have the potential to be used as antisense therapies since they are expected to enhance nuclease resistance and cellular uptake while they maintain sequence-specificity and affinity to nucleic acid targets in vitro or in vivo.

  本文披露了一些改性核苷酸，由改性糖基组成，其中包含在脱氧核糖或核糖的C1和C4位置具有取代基，或在C3和C5位置具有支链取代基。每个核苷酸被转化或适当保护，然后转化为相应的磷酰胺酯。这些磷酰胺酯用于组装寡核苷酸，在其中至少有一个前述的核苷酸。这些糖基改性的寡核苷酸具有作为反义疗法的潜力，因为它们预计能够增强核酸酶抵抗力和细胞摄取能力，同时在体外或体内保持序列特异性和亲和力与核酸靶标。
• Incorporation of 3′-C-(Hydroxymethyl)thymidine into novel oligodeoxynucleotide analogues
  作者：Pia Nørregaard Jørgensen、Margit L. Svendsen、Claus Scheuer-Larsen、Jesper Wengel

  DOI：10.1016/0040-4020(94)01089-i

  日期：1995.2

  3′-C-(Hydroxymethyl)thymidine (1) has been incorporated into novel oligodeoxynucleotide (ODN) analogues containing extended (Y, 5′-hydroxyl to 3′-hydroxymethyl) backbones using the phosphoramidite building block 4. The hybridization properties and enzymatic stabilities were studied by UV experiments. ODNs containing the modified nucleotide Y exhibited minor decreases in the affinity towards complementary

  3'- C-（羟甲基）胸苷（1）已使用亚磷酰胺结构单元4掺入了含有扩展的（Y，5'-羟基至3'-羟甲基）主链的新型寡脱氧核苷酸（ODN）类似物。通过UV实验研究了杂交特性和酶稳定性。含有修饰的核苷酸Y的ODN对互补DNA的亲和力显示出较小的下降，但是通过评估含有相应类似修饰的N 3-甲基核苷酸Z的ODN，支持了涉及修饰的核苷酸Y的Watson-Crick碱基配对。获得的结果将Y与包含1个具有未修饰主链（X，5'-至3'-羟基）的ODN进行比较。
• 3'-C-Hydroxymethylthymidine: Synthesis and Incorporation into Oligodeoxynucleotide Analogues
  作者：Pia Nøncgaard Jørgensen、Margit Svendsen、Claus Nielsen、Jesper Wengel

  DOI：10.1080/15257779508012502

  日期：1995.5.1

  The stereoselective synthesis of 3'-C-hydroxymethylthymidine (5) in five steps from thymidine has been accomplished and this nucleoside has been incorporated into oligodeoxynucleotides (ODNs) in different ways.
• Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-<i>C</i>-Aminomethyl-and 3′-<i>C</i>-Amethylthymidine
  作者：Guangyi Wang、Patrick J. Middleton、Liyan He、Vesna Stoisavljevic、Wiliiied E. Seifert

  DOI：10.1080/07328319708001361

  日期：1997.4

  3'-C-Aminomethyl- and 3'-C-methylthymidine were synthesized and incorporated into oligodeoxynucleotides. Hybridization and enzyme stability of the modified oligonucleotides containing the 3'-C-branched thymidines are discussed.
• US5712378A
  申请人：——

  公开号：US5712378A

  公开（公告）日：1998-01-27