3',5'-O-(Di-tert-butylsilanediyl)cytidine | 126628-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-O-(Di-tert-butylsilanediyl)cytidine
• 英文别名: 4-Amino-1-((4aR,6R,7R,7aS)-2,2-di-tert-butyl-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl)pyrimidin-2(1H)-one；1-[(4aR,6R,7R,7aS)-2,2-ditert-butyl-7-hydroxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-4-aminopyrimidin-2-one
• CAS: 126628-28-2
• 化学式: C₁₇H₂₉N₃O₅Si
• 分子量: 383.52
• InChiKey: USTPVWPEVXRNDY-FMKGYKFTSA-N

物化性质

• 沸点：
  525.0±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',5'-O-(Di-tert-butylsilanediyl)cytidine 在 吡啶 、 咪唑 、 1,3-二氯-5,5-二甲基海因 、 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 75.92h， 生成 triethylamine 4-(4-((((2R,3R,4R,5R)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl)oxy)diisopropylsilyl)benzamido)butanoate
  参考文献：
  名称：

  Chemical Synthesis of U1 snRNA Derivatives

  摘要：

  U1 snRNA is an interesting biological tool for splicing correction and regulation of gene expression. However, U1 snRNA has never been chemically synthesized. In this study, the first chemical synthesis of U1snRNA and its analogues was carried out. Moreover, it was found that the binding affinity of the modified U1 snRNA with an ethylene glycol linkage to snurportin 1 (nuclear import adaptor) was as high as that of the unmodified RNA.

  DOI：

  10.1021/ol401917r
• 作为产物：
  描述：

  二叔丁基氯硅烷 、 胞苷 在 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以100%的产率得到3',5'-O-(Di-tert-butylsilanediyl)cytidine
  参考文献：
  名称：

  Synthesis of 2‘-C-α-(Hydroxyalkyl) and 2‘-C-α-Alkylcytidine Phosphoramidites:  Analogues for Probing Solvent Interactions with RNA

  摘要：

  Nucleoside analogues bearing 2'-C-alpha-(hydroxyalkyl) and 2'-C-alpha-alkyl substitutes have numerous applications in RNA chemistry and biology. In particular, they provide a strategy to probe the interaction between the 2'-hydroxyl group of RNA and water. To incorporate these nucleoside analogues into oligonucleotides for studies of the group II intron (Gordon, P. M.; Fong, R.; Deb, S.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237), we synthesized six new phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-(hydroxyalkyl)cytidine (36: R = -(CH2)(2)OH; 38: R = -(CH2)(3)OH; 40: R = -(CH2)(4)OH) and 2'-deoxy-2'-C-alpha-alkylcytidine (37: R = -CH2CH3; 39: R = -(CH2)(2)CH3; 41: R = -(CH2)(3)CH3) from cytidine or uridine via 2'-C-alpha-allylation, followed by alkene and alcohol transformations. Phosphoramidites 36 and 37 were prepared from cytidine in overall yields of 14% (10 steps) and 7% (11 steps), respectively. Phosphoramidites 38 and 39 were prepared from uridine in overall yields of 30% (10 steps) and 13% (11 steps), respectively. Phosphoramidites 40 and 41 were synthesized from uridine in overall yields of 21% (13 steps) and 25% (14 steps), respectively.

  DOI：

  10.1021/jo062002t

文献信息

• An efficient preparation of protected ribonucleosides for phosphoramidite RNA synthesis
  作者：Vladimir Serebryany、Leonid Beigelman

  DOI：10.1016/s0040-4039(02)00181-8

  日期：2002.3

  An efficient synthesis of protected ribonucleosides useful for phosphoramidite RNA synthesis is described. Di-t-butylsilylene group was employed for simultaneous protection of 3′- and 5′-hydroxyl functions of nucleoside. Subsequent silylation of free 2′-OH group followed by introduction of suitable protection on the base moiety, removal of cyclic silyl protection and tritylation of 5′-OH gave target

  描述了可用于亚磷酰胺RNA合成的受保护的核糖核苷的有效合成。二吨-butylsilylene组用于和的3'-保护同时核苷的5'位羟基的功能。随后将游离的2'-OH基团进行甲硅烷基化，然后在碱基部分上引入适当的保护，除去环甲硅烷基的保护基团并进行5'-OH的三苯甲基化反应，目标化合物的总收率为60-66％。
• Synthesis of 2′-<i>O</i>-Substituted Ribonucleosides
  作者：V. Serebryany、L. Beigelman

  DOI：10.1081/ncn-120022724

  日期：2003.10

  efficient synthesis of 2'-O-substituted ribonucleosides, including 2'-O-TBDMS and 2'-O-TOM protected as well as 2'-O-Me and 2'-O-allyl derivatives is presented. Di-t-butylsilylene group was employed for simultaneous protection of 3'- and 5'- hydroxyl functions of nucleoside on the first step. Subsequent silylation or alkylation of free 2'-OH followed by introduction of suitable protection on the base

  提出了2'-O-取代的核糖核苷的有效合成方法，包括2'-O-TBDMS和受保护的2'-O-TOM以及2'-O-Me和2'-O-烯丙基衍生物。第一步，使用二叔丁基亚甲硅烷基同时保护核苷的3'-和5'-羟基官能团。随后将游离的2'-OH进行甲硅烷基化或烷基化，然后在碱基部分上引入合适的保护基，并除去环状甲硅烷基保护基，从而以高收率得到目标化合物。
• Site-Specific Synthesis of <i>N</i>⁴-Acetylcytidine in RNA Reveals Physiological Duplex Stabilization
  作者：David Bartee、Kellie D. Nance、Jordan L. Meier

  DOI：10.1021/jacs.1c11985

  日期：2022.3.2

  post-transcriptional modification of RNA that is conserved across all domains of life. All characterized sites of ac4C in eukaryotic RNA occur in the central nucleotide of a 5′-CCG-3′ consensus sequence. However, the thermodynamic consequences of cytidine acetylation in this context have never been assessed due to its challenging synthesis. Here, we report the synthesis and biophysical characterization

  N4-乙酰胞苷 （ac4C） 是 RNA 的转录后修饰，在生命的所有领域中都是保守的。真核 RNA 中 ac4C 的所有特征位点都发生在 5'-CCG-3' 共有序列的中心核苷酸中。然而，由于其具有挑战性的合成，在这种情况下胞苷乙酰化的热力学后果从未被评估过。在这里，我们报道了 ac4C 在其内源性真核序列背景下的合成和生物物理表征。首先，我们开发了一种合成路线，用于含有亲电乙酰基团的均相 RNA。接下来，我们使用热变性来研究 ac4C 对人类 rRNA 中发现的天然序列中双链体稳定性和错配鉴别的生化影响。最后，我们证明了这种化学方法能够将 ac4C 整合到人类 tRNA 的复杂修饰景观中，并使用双链体熔解来强调 ac4C 在这种独特序列背景下的强制作用。通过在生理序列背景下对核酸乙酰化进行离体生物物理分析，这些研究为理解普遍保守的核碱基在生物学和疾病中的功能奠定了化学基础。
• Furusawa, Kiyotaka; Ueno, Katsuhiko; Katsura, Tatsuo, Chemistry Letters, 1990, p. 97 - 100
  作者：Furusawa, Kiyotaka、Ueno, Katsuhiko、Katsura, Tatsuo

  DOI：——

  日期：——
• FURUSAWA, KIYOTAKA;UENO, KATSUHIKO;KATSURA, TATSUO, CHEM. LETT.,(1990) N, C. 97-100
  作者：FURUSAWA, KIYOTAKA、UENO, KATSUHIKO、KATSURA, TATSUO

  DOI：——

  日期：——