3',5'-Di-O-benzoyl-2'-deoxyuridine

• 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: 3',5'-Di-O-benzoyl-2'-deoxyuridine
• 英文别名: 3',5'-Di-O-benzoyl-2'-desoxy-uridin；[(2R,3S,5R)-3-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• 化学式: C₂₃H₂₀N₂O₇
• 分子量: 436.421
• InChiKey: WTTRUBICDWFROZ-NLWGTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-Di-O-benzoyl-2'-deoxyuridine 在 甲醇 、 氨 作用下， 反应 6.0h， 以65%的产率得到5'-O-Benzoyl-2'-desoxy-β-D-ribofuranosyluracil
  参考文献：
  名称：

  完全苯甲酰化核苷衍生物的选择性脱保护

  摘要：

  苯甲酰化羟基的选择性脱保护是核苷类似物以及其他多官能分子合成中的关键问题之一。

  DOI：

  10.1081/car-200030095
• 作为产物：
  描述：

  2'-脱氧胞苷盐酸盐 在 吡啶 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 15.0h， 生成 3',5'-Di-O-benzoyl-2'-deoxyuridine
  参考文献：
  名称：

  Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

  摘要：

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

  DOI：

  10.1021/ol0518378

文献信息

• A general method for N-glycosylation of nucleobases promoted by (p-Tol)₂SO/Tf₂O with thioglycoside as donor
  作者：Guang-jian Liu、Xiao-tai Zhang、Guo-wen Xing

  DOI：10.1039/c5cc03617h

  日期：——

  35 nucleosides were synthesized by coupling thioglycosides with pyrimidines and purines under the preactivation of (p-Tol)₂SO/Tf₂O in high yields and with β-stereoselectivities.

  35个核苷酸通过在高产率和β-立体选择性下，在（p-Tol）2SO/Tf2O的预活化下，将硫代糖苷与嘧啶和嘌呤偶联合成。
• Continuous flow photocatalysis enhanced using an aluminum mirror: rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides
  作者：Bo Shen、Matthew W. Bedore、Adam Sniady、Timothy F. Jamison

  DOI：10.1039/c2cc33356b

  日期：——

  reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2'-deoxy and 2',3'-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

  已经开发出一种具有石英管，铝镜和温度控制装置的独特光化学流反应器，用于光诱导的电子转移脱氧反应，以产生2'-脱氧和2'，3'-二脱氧核苷。连续流形式显着提高了反应的效率和选择性。
• Lipase-catalyzed regioselective acylation of sugar moieties of nucleosides
  作者：Atsuhiko Uemura、Kenji Nozaki、Jun-ichi Yamashita、Mitsugi Yasumoto

  DOI：10.1016/s0040-4039(01)80665-1

  日期：1989.1

  A regioselective acylation of 2′-deoxypyrimidine nucleosides by an acid anhydride in a dry polar aprotic solvent is catalyzed by a lipase from Pseudomonas fluorescenbce.

  在干燥的极性非质子传递溶剂中，酸酐对2'-脱氧嘧啶核苷的区域选择性酰化反应由荧光假单胞菌（Pseudomonas fluorescenbce）的脂肪酶催化。
• Palladium-catalyzed cross-coupling of trifluoroisopropenylzinc reagent with vinyl halides. A novel stereospecific of trifluoromethylated 1,3-dienes
  作者：Jiang Biao、Xu Yuanyao

  DOI：10.1016/s0040-4039(00)93982-0

  日期：1992.1

  1,3-Dienes containing a CF3-group were stereospecifically synthesized via palladium-catalyzed cross-coupling of trifluoroiso-propenylzinc reagent with vinyl halides in high yields. A novel CF3-containing nucleoside, 5-(α-CF3-ethenyl)-2′-deoxyuridine (6) was prepared via this methodology.

  通过钯催化三氟异丙烯基锌试剂与乙烯基卤化物的交叉偶联，高产率地立体合成了含有CF 3-基团的1，3-二烯。一种新颖的CF 3含核苷，5-（α-CF 3 -乙烯基）-2'-脱氧尿苷（6）通过这种方法制备。
• Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides
  作者：Zhiwei Wang、Daniel R. Prudhomme、Jason R. Buck、Minnie Park、Carmelo J. Rizzo

  DOI：10.1021/jo0003652

  日期：2000.9.1

  arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrüggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer

  描述了β2'-脱氧-，α2'-脱氧-，β3'-脱氧-和β2'，3'-脱氧核糖核苷的立体控制的从头合成。合成了具有战略指导意义的受保护的核糖，阿拉伯糖和木糖糖基化前体，它们带有能够指导Vorbrüggen糖基化的C2-酯。关键步骤是所需羟基作为苯甲酰基-或3-（三氟甲基）苯甲酰基衍生物的区域选择性脱氧。该脱氧是通过使用咔唑衍生物作为光敏剂的光诱导电子转移（PET）机制完成的。所需脱氧核苷的合成通常从一个容易获得的常见前体分三步进行。