2',3',5'-tris-O-(trimethylsilyl)uridine | 10457-16-6

• 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: 2',3',5'-tris-O-(trimethylsilyl)uridine
• 英文别名: TMS(-2)[TMS(-3)][TMS(-5)]Ribf(b)-uracil-1-yl；1-[(2R,3R,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 10457-16-6
• 化学式: C₁₈H₃₆N₂O₆Si₃
• 分子量: 460.75
• InChiKey: PMTYSPPFEFHVGD-MWQQHZPXSA-N

物化性质

• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',3',5'-tris-O-(trimethylsilyl)uridine 在 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 8.25h， 生成 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521
• 作为产物：
  描述：

  三甲基氯硅烷 、 尿嘧啶核苷 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2',3',5'-tris-O-(trimethylsilyl)uridine
  参考文献：
  名称：

  二硫键稳定的RNA发夹的合成

  摘要：

  一个Ñ -3的RNA发夹的乙硫醇改性的尿苷已经合成，并通过固相亚磷酰胺化学结合在5'和3'末端，以通过二硫键交联提供增加的构象稳定性。

  DOI：

  10.1016/0040-4039(94)88309-2

文献信息

• Synthesis and stability of S-cyanoethyl-protected 4-thiouridine and 2′-deoxy-4-thiouridine
  作者：Robert S. Coleman、James M. Siedlecki

  DOI：10.1016/0040-4039(91)80679-z

  日期：1991.6

  A convenient preparation of S-(2-cyanoethyl) protected 2′-deoxy-4-thiouridine (5a) and 4-thiouridine (5b) is presented. The S-cyanoethyl protecting group is stable to reagents commonly encountered during the phosphoramidite method of solid-phase oligonucleotide synthesis, and is readily deprotected using concentrated NH4OH at 25°C.

  提出了方便的制备S-（2-氰乙基）保护的2'-脱氧-4-硫尿苷（5a）和4-硫尿苷（5b）的方法。该小号氰乙基保护基团是稳定的固相寡核苷酸合成的亚磷酰胺方法中通常遇到的试剂，并使用浓NH容易脱保护4 OH在25℃下。
• Synthesis of 4-Thiouridine, 6-Thioinosine, and 6-Thioguanosine 3‘,5‘-<i>O</i>-Bisphosphates as Donor Molecules for RNA Ligation and Their Application to the Synthesis of Photoactivatable TMG-Capped U1 snRNA Fragments
  作者：Michinori Kadokura、Takeshi Wada、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/jo991432z

  日期：2000.8.1

  S-(2-cyanoethyl)thionucleosides were converted to the 2'-O-(tert-butyldimethylsilyl)ribonucleoside 3'-phosphoramidite derivatives 7, 18, and 26 or 3',5'-bisphosphate derivatives 8, 19, and 27. Treatment of 8, 19, and 27 with DBU gave thionucleoside 3',5'-bisphosphate derivatives 9, 20, and 28, which were found to be substrates of T4 RNA ligase. These thionucleoside 3',5'-bisphosphates were examined as donors for

  通过显着改进的方法以高收率合成了4-硫代尿苷，6-硫鸟嘌呤和6-硫代肌苷3'，5'-双磷酸酯（9、20和28）。在前两种化合物中，尿苷和2-N-苯基乙酰鸟苷通过瞬时O-三甲基甲硅烷基化反应转化为相应的4-和6-O-苯磺酰基中间体（2和13），然后使它们与2-反应。氰基乙硫醇在N-甲基吡咯烷存在下分别得到4-硫代尿苷（3）和2-N-苯基乙酰基-6-硫代鸟苷衍生物（14）。这些硫代核苷衍生物的原位二甲氧基三苯甲基化从1和11产生5'掩蔽的产物4和15的高总收率。6-S-（2-氰乙基）-5'-O-（4,4'-二甲氧基三苯甲基）- 6-硫代肌苷（23）通过5'的取代合成 -O-三苯甲基化的6-氯嘌呤核糖苷衍生物22与2-氰基乙硫醇。这些S-（2-氰基乙基）硫代核苷被转化为2'-O-（叔丁基二甲基甲硅烷基）核糖核苷3'-亚磷酰胺衍生物7、18和26或3'，5'-双磷酸酯衍生物8、19和27用DBU处
• Mild, effective and selective method for the silylation of alcohols using silazanes promoted by catalytic tetrabutylammonium fluoride
  作者：Yoo Tanabe、Masanari Murakami、Kazuto Kitaichi、Yoshihiro Yoshida

  DOI：10.1016/s0040-4039(00)74419-4

  日期：1994.11

  The presence of catalytic amounts (∼0.02 equiv.) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols using a variety of available silazanes under mild conditions with high chemoselectivity, wherein the choice of silazanes allowed an alternative method for the powerful silylation of various kinds of alcohols or the highly regioselective silylation of primary alcohols

  催化量（〜0.02当量）的四丁基氟化铵（TBAF）在温和的条件下以高化学选择性显着促进了使用各种可用的硅氮烷的醇甲硅烷基化，其中选择硅氮烷可以实现强力甲硅烷基化的另一种方法各种醇或伯醇的高度区域选择性甲硅烷基化。
• An Improved Transient Method for the Synthesis of<i>N</i>-Benzoylated Nucleosides
  作者：Xue-Feng Zhu、Howard J. Williams、A. Ian Scott

  DOI：10.1081/scc-120017200

  日期：2003.1.5

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
• Zhou, Xiao-Xiong; Ugi, Ivar; Chattopadhyaya, Jyoti, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 9, p. 761 - 766
  作者：Zhou, Xiao-Xiong、Ugi, Ivar、Chattopadhyaya, Jyoti

  DOI：——

  日期：——