6-hydroxymethyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-deoxyuridine | 98495-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-hydroxymethyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-deoxyuridine
• 英文别名: 1-[(6aR,8R,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-6-(hydroxymethyl)pyrimidine-2,4-dione
• CAS: 98495-61-5
• 化学式: C₂₂H₄₀N₂O₇Si₂
• 分子量: 500.74
• InChiKey: RULVKRODKHEOAC-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-hydroxymethyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-deoxyuridine 在 三甲基溴硅烷 、 碘苯二乙酸 、 碘 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 9.0h， 生成 (6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one
  参考文献：
  名称：

  C-1′ Radical-Based Approaches for the Synthesis of Anomeric Spironucleosides

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2866::aid-chem2866>3.0.co;2-6
• 作为产物：
  描述：

  1-[3,5-Bis-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)-2-deoxy-β-D-erythro-furanosyl]uracil-6-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以53%的产率得到6-hydroxymethyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-deoxyuridine
  参考文献：
  名称：

  Synthesis of Anomeric Spiro Uracil Nucleosides with an Orthoester Structure: Stereoselective Cyclization Controlled by the C6-Substituent

  摘要：

  Uracil nucleosides having an anomeric orthoester structure were synthesized fi om 2'-deoxy-6-(hydroxyalkyl)uridines through hypoiodite-initiated cyclization. The hydroxyalkyl substituent at the 6-position was found to control the anomeric stereochemistry (beta/alpha=7/1 similar to 1/46) of the cyclization. The transition state geometry of the reaction was postulated based on the X-ray crystallographic structure of the cyclized product 7 alpha to elucidate the observed stereoselectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01486-x

文献信息

• A new class of anomeric spironucleosides
  作者：Thanasis Gimisis、Chryssostomos Chatgilialoglu、Thanasis Gimisis、Carlo Castellari

  DOI：10.1039/a705742c

  日期：——

  A 1,5-hydrogen migration of a conveniently situated alkoxyl radical affords spironucleosides which possess an unusual orthoamide structure at the anomeric position; X-ray crystallography establishes the configuration of the C-1′ position.

  通过方便位于的烷氧自由基的1,5-氢迁移得到了螺核苷，这些螺核苷在异头位置具有一种不寻常的邻酰胺结构；X射线晶体学确立了C-1'位置的构型。
• Lithiation of 3',5'--(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine: synthesis of 6-substituted 2'-deoxyuridines
  作者：Hiromichi Tanaka、Hiroyuki Hayakawa、Shuji Iijima、Kazuhiro Haraguchi、Tadashi Miyasaka

  DOI：10.1016/s0040-4020(01)96402-6

  日期：1985.1

  Synthesis of 6-substituted 2'-deoxyuridines can be effected by lithiation of 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine with LDA followed by the reaction of its lithio derivative with electrophiles. This method provides a general, regiospecific and simple route to various types of 6-substituted 2'-deoxyuridines which have, so far, been known to be difficult to prepare.

  6-取代的2'-脱氧尿苷的合成可以通过将3'，5'-O-（四异丙基二硅氧烷-1,3-二基）-2'-脱氧尿苷与LDA锂化，然后使其硫代衍生物与亲电试剂反应来进行。该方法提供了一般的，区域特异性的和简单的途径来制备迄今已知难以制备的各种类型的6-取代的2'-脱氧尿苷。
• 6-azido and 6-azidomethyl uracil nucleosides
  作者：Yahaira Reyes、Alexander Mebel、Stanislaw F. Wnuk

  DOI：10.1080/15257770.2023.2271023

  日期：2024.5.3

  Azido nucleosides have been utilized for click reactions, metabolic incorporation into cellular DNA, and fluorescent imaging of live cells. Two classes of 6-azido modified uracil nucleosides; one w...

  叠氮核苷已用于点击反应、代谢掺入细胞 DNA 以及活细胞的荧光成像。两类6-叠氮基修饰的尿嘧啶核苷；一瓦...