2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine | 81243-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
• 英文别名: 1-[(6aR,8R,9R,9aR)-9-(oxan-2-yloxy)-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]pyrimidine-2,4-dione
• CAS: 81243-97-2
• 化学式: C₂₆H₄₆N₂O₈Si₂
• 分子量: 570.831
• InChiKey: HEFDGHJCGVOAHF-IKKTWZKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  110.24
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 在 potassium fluoride 、 1,3-dimethoxy-benzene-(sulphonyl)-2,4-disulfonyl chloride 、 四乙基溴化铵 、 次磷酸 作用下， 以 吡啶 、 水 、 乙腈 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  利用S，S-二苯基n-单甲氧基三苯甲基三核糖核苷3'-phosphodiodithioates合成寡核糖核苷酸

  摘要：

  经过5步或6步反应，完全保护的核糖核苷酸单元（6a–d）的总产率为42–62％。将二甲氧基三苯甲基，单甲氧基三苯甲基，四氢吡喃-2-基和苯硫基分别引入到5'-OH，外-氨基，2'-OH和3'-磷酰基官能团上。通过用三氟乙酸或次膦酸-三乙胺处理，将单元转化为OH或磷酸二酯组分。借助于均三甲苯二甲磺酰氯3-硝基-1,2,4-三唑适当地偶联两种组分，以高收率得到二聚体。该方法已成功应用于GpUpApUpUpApApUpAp的合成，即溴化花叶病毒4号RNA细丝的5'端碱基序列。

  DOI：

  10.1016/0040-4020(84)85114-5
• 作为产物：
  描述：

  O^2'-tetrahydropyran-2-yl-uridine 生成 2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  KIERZEK, R.;MARKIEWICZ, W. T.;IMIOLCZYK, B., BIOPHOSPHAT. AND ANALOGUES: SYNTH., STRUCT. METAB. AND ACTIV. PROC. 2ND I+

  摘要：

  DOI：

文献信息

• Chemical Synthesis of Capped Oligoribonucleotides, m⁷G^5′pppAUG and m⁷G^5′pppAUGACC
  作者：Mitsuo Sekine、Shin-ichi Nishiyama、Takashi Kamimura、Yumi Osaki、Tsujiaki Hata

  DOI：10.1246/bcsj.58.850

  日期：1985.3

  The fully-protected pAUG (15) and pAUGACC (21) were synthesized by the phosphotriester approach where the phenylthio group was employed as the internal and 5′-terminal phosphate-protecting groups. The partially unblocked oligomers (32) and (33), obtained by alkaline treatment of (15) and (21), were condensed with a capping reagent (1a) in the presence of imidazole by activation with silver nitrate to afford the capped trimer and hexamer protected with the acid-labile protecting groups, i.e., 4,4,′4″-trimethoxytrityl (TMTr), 4-monomethoxytrityl (MMTr), tetrahydropyran-2-yl (THP), and methoxymethylene (mM) groups. The protected capped oligomers were unblocked by a dilute HCl solution to afford m7G5′ pppAUG and m7G5′ pppAUGACC, which were purified by HPLC and characterized by enzyme assays.

  采用磷酯化方法合成了完全保护的pAUG (15)和pAUGACC (21)，其中苯硫基用作内部和5′-末端磷酸保护基团。通过(15)和(21)的碱性处理获得了部分未封闭的寡聚物(32)和(33)，在咪唑存在下，用硝酸银活化，与封端试剂(1a)缩合，得到用酸不稳定保护基团保护的封端三聚体和六聚体，即4,4,′4″-三甲氧基三苯甲基(TMTr)、4-单甲氧基三苯甲基(MMTr)、四氢吡喃-2-基(THP)和甲氧基甲烯基(MM)基团。用稀盐酸溶液解除保护封端的寡聚物，得到m7G5′ pppAUG和m7G5′ pppAUGACC，通过HPLC纯化，并通过酶测定进行表征。
• Markiewicz, Wojciech T.; Biala, Ewa; Kierzek, Ryszard, Bulletin of the Polish Academy of Sciences: Chemistry, 1984, vol. 32, # 11-12, p. 433 - 451
  作者：Markiewicz, Wojciech T.、Biala, Ewa、Kierzek, Ryszard

  DOI：——

  日期：——
• RNA Modified Uridines VII: Chemical Synthesis and Initial Analysis of tRNA D-Loop Oligomers with Tandem Modified Uridines
  作者：Barbara Nawrot、Andrzej Malkiewicz、Wanda S. Smith、Hanna Sierzputowska-Gracz、Paul F. Agris

  DOI：10.1080/15257779508014659

  日期：1995.2

  The first chemical synthesis of oligoribonucleotides with adjacent and significantly different modified uridines, the hydrophobic dihydrouridine, D, and the hydrophilic 3-[3-(S)-amino-3-carboxypropyl]-uridine, (acp)U-3, is reported. The trimers Dp-acp(3)UpA, Up-acp(3)UpA, DpUpA and UpUpA, and the dimer Dp-acp(3)U were synthesized and initial structural analysis performed. The synthesis included a combination of protecting groups that is generally applicable to oligonucleotide syntheses in combination with various 2'OH protecting groups. The protecting groups did not cause racemization of the amino acid residue of (acp)3U during deprotection. The assignment of all H-1 NMR resonances of modified nucleoside-containing oligoribonucleotides includes heteronuclear one and two dimensional NMR.
• Kierzek, Ryszard; Markiewicz, Wojciech T., Bulletin of the Polish Academy of Sciences: Chemistry, 1990, vol. 38, # 1-12, p. 29 - 36
  作者：Kierzek, Ryszard、Markiewicz, Wojciech T.

  DOI：——

  日期：——
• The Stability of Trisubstituted Internucleotide Bond in the Presence of the Vicinal 2′-Hydroxyl. Chemical Synthesis of Uridyl(2′-phosphate)-(3′-5′)-uridine
  作者：R. Kierzek

  DOI：10.1080/15257779408009478

  日期：1994.9

  The effect of eleven different phosphoryl center protecting groups on the stability of trisubstituted internucleotide bond of the dimers (1a-k), in the presence of the vicinal 2'-hydroxyl, was examined. It has been found that electronic properties of the phosphoryl center protecting groups are essential for the reactivity of the trisubstituted internucleotide bond. Those observations were applied to the chemical synthesis of the uridyl(2'-phosphate)-(3'-5')-uridine, a useful model for further pre-tRNA splicing studies.