1,3-dimethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine | 80545-43-3

• 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: 1,3-dimethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine
• 英文别名: 1,3-Dimethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxanyl)-ψ-uridine；1,3-dimethyl-3',5'-O-(tetraisopropyldisiloxanyl)pseudouridine；5-[(6aR,8S,9S,9aS)-9-hydroxy-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]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 80545-43-3
• 化学式: C₂₃H₄₂N₂O₇Si₂
• 分子量: 514.767
• InChiKey: VRJINNALHIGZER-IVAOSVALSA-N

物化性质

• 沸点：
  520.3±60.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine 在 吡啶 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(5aS,6S,8R,8aR)-6-(1,3-dimethyl-2,4-dioxopyrimidin-5-yl)-2,2,4,4-tetra(propan-2-yl)-5a,6,8,8a-tetrahydrofuro[3,4-f][1,3,5,2,4]trioxadisilepin-8-yl]methyl acetate
  参考文献：
  名称：

  核苷。130。2'-脱氧-2'-取代的和5'-脱氧-5'-取代的-ψ-尿苷衍生物的合成。2′-氯-2′-脱氧-1，3-二甲基-ψ-尿苷的结晶和分子结构。指导合成2'-脱氧-2'-取代的阿拉伯糖核苷的研究。1 †

  摘要：

  开发了一种从3'，5'- O-（1，1，3，3-四异丙基二硅氧烷基）-1,3-二甲基-ψ-制备5'-脱氧-5'-取代-ψ-尿苷衍生物4的方法尿苷1通过甲硅烷基重排反应。2' - O-甲磺酰基-1,3-二甲基-ψ-尿苷7的甲磺酰氧基功能的亲核取代提供了带有2'-取代基的“向下”核糖构型的产品8。2'-氯衍生物8a的X射线晶体学分析牢固地建立了8的分子结构，并为相邻基团参与7的4-羰基官能团提供了证据。 在亲核反应中。

  DOI：

  10.1002/jhet.5570220646
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 1,3-二甲基假尿苷 在 吡啶 作用下， 反应 4.0h， 以97%的产率得到1,3-dimethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine
  参考文献：
  名称：

  Nucleosides. 121. Improved and general synthesis of 2'-deoxy-C-nucleosides. Synthesis of 5-(2-deoxy-.beta.-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine

  摘要：

  DOI：

  10.1021/jo00342a022

文献信息

• A Facile Synthesis of the Phosphoramidites of 2-<i>N</i>-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1, 3-Dimethyl-2′-deoxy-ψ-uridine and<i>N</i>1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis
  作者：B. K. Bhattacharya、G. R. Revankar

  DOI：10.1080/15257779408009476

  日期：1994.9

  An efficient and facile syntheses of 5'-O-(4,4'-dimethoxytrityl)-3'-[2-cyanoethyl bis(1-methylethyl)]phosphoramidites of 2-N-methyl-2'-deoxy-psi-isocytidine (h), 2-N-methyl-2'-deoxy-alpha-psi-isocytidine (13 ), 2-N-methyl-2'-O-allyl-psi-isocytidine (11), 1,3-dimethyl-2'-deoxy-psi-uridine (4) and N1-methyl-2'-O-allyl-psi-uridine (19) have been accomplished in good overall yields. The pyrimidine-pyrimidine transformation reaction was found to be useful for the preparation of 2-N-methyl-2'-O-allyl-psi-isocytidine (10). The utility of these novel phosphoramidites is demonstrated by their incorporation into oligonucleotides via solid-support, oligonucleotide methodology.
• Triplex formation of an oligonucleotide containing 2'-O-methylpseudoisocytidine with a DNA duplex at neutral pH
  作者：Akira Ono、Paul O. P. Ts'o、Lou Sing Kan

  DOI：10.1021/jo00037a048

  日期：1992.5

  The synthesis of the hexadecanucleotide 5'TTTT1TTTT111111T3' (1-16mer) containing 2-amino-5-(2-O-methyl-beta-D-ribofuranosyl)-4(1H)-pyrimidinone (2'-O-methylpseudoisocytidine or 1) is described. Triplex formation of 1-16mer with a deoxyribonucleotide duplex 5'd(ACCAAAAGAAAAGGGGGGACCA)3'-5'd-(TGGTCCCCCCTTTTCTTTTGGT)3' (duplex-22) which contains the "polypurine tract" found in the genome of human T-cell leukaemia (lymphotropic) virus (HTLV-III) was studied by thermal denaturation and circular dichroiam (CD) spectra in aqueous solution at neutral pH. The "polypurine tract" contains a homoguanine cluster consisting of 6 deoxyguanine residues. The results indicate that 1-16mer and duplex-22 formed a triplex at neutral condition (0.01 M Na cacodylate, 0.5 M NaCl, 5 mM MgCl2, pH 7.2. T(m) = 20-degrees-C). In contrast, a hexadecadeoxynucleotide, 5'TTTTMTTTTMMMMMMT3'(M-16mer), containing 5-methyl-2-deoxycytidine (M) did not form a stable triplex with duplex-22 at the same condition (T(m) < 0-degrees-C). The CD mixing titration indicated that the triplex was formed with 1:1 (duplex:third strand) molecular stoichiometry.
• Nucleosides. 121. Improved and general synthesis of 2'-deoxy-C-nucleosides. Synthesis of 5-(2-deoxy-.beta.-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine
  作者：Krzysztof Pankiewicz、Akira Matsuda、Kyoichi A. Watanabe

  DOI：10.1021/jo00342a022

  日期：1982.1
• Nucleosides.<b>130</b>. Synthesis of 2′-Deoxy-2′-substituted- and 5′-Deoxy-5′-substituted-ψ-uridine Derivatives. Crystalline and Molecular Structure of 2′-Chloro-2′-deoxy-1,3-dimethyl-ψ-uridine. Studies Directed Toward the Synthesis of 2′-Deoxy-2′-substituted-<i>arabino</i>-Nucleosides.<b>1</b>
  作者：Krzysztof W. Pankiewicz、Kyoichi A. Watanabe、Hiroaki Takayanagi、Tsueno Itoh、Haruo Ogura

  DOI：10.1002/jhet.5570220646

  日期：1985.11

  5′-deoxy-5′-substituted-ψ-uridine derivatives 4 from 3′,5′-O-(1, 1, 3, 3-tetraisopropyldisiloxanyl)-1,3-dimethyl-ψ-uridine 1 via a silyl rearrangement reaction. Nucleophilic displacement of the mesyloxy function of 2′-O-mesyl-1,3-dimethyl-ψ-uridine 7 afforded products with the 2′-substituent in the “down” ribo configuration 8. X-Ray crystallographic analysis of the 2′-chloro derivative 8a firmly established the

  开发了一种从3'，5'- O-（1，1，3，3-四异丙基二硅氧烷基）-1,3-二甲基-ψ-制备5'-脱氧-5'-取代-ψ-尿苷衍生物4的方法尿苷1通过甲硅烷基重排反应。2' - O-甲磺酰基-1,3-二甲基-ψ-尿苷7的甲磺酰氧基功能的亲核取代提供了带有2'-取代基的“向下”核糖构型的产品8。2'-氯衍生物8a的X射线晶体学分析牢固地建立了8的分子结构，并为相邻基团参与7的4-羰基官能团提供了证据。 在亲核反应中。