2,3,5-tri-O-benzyl-α,β-D-ribofuranosy fluoride | 114762-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzyl-α,β-D-ribofuranosy fluoride
• 英文别名: 2,3,5-tri-O-benzyl-1-fluoro-D-ribofuranose；(3R,4R,5R)-2-fluoro-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 114762-38-8
• 化学式: C₂₆H₂₇FO₄
• 分子量: 422.496
• InChiKey: XRTVLEDCQXWQBB-NITSXXPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-α,β-D-ribofuranosy fluoride 、 4-氯苯基溴化镁 以 四氢呋喃 为溶剂， 以67%的产率得到(2S,3S,4R,5R)-2-(4-chlorophenyl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
  参考文献：
  名称：

  Simple Synthesis of Aromatic β-C-Nucleosides via Coupling of Aryl Grignard Reagents with Sugar Fluorides

  摘要：

  过苄基化的d-核糖呋喃糖氟化物与芳香杂环如噻吩、吡咯和吲哚的格林纳试剂在THF中反应，得到相应的β-C-核苷，产率中等。该过程也可应用于过苄基化的d-葡萄糖吡喃糖氟化物和过苄基化的2-脱氧-d-核糖呋喃糖氟化物作为糖供体。

  DOI：

  10.1055/s-1998-4487
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 二乙胺基三氟化硫 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到2,3,5-tri-O-benzyl-α,β-D-ribofuranosy fluoride
  参考文献：
  名称：

  A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using dast. Preparation of glycosyl fluorides.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98451-x

文献信息

• Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole <i>C</i>-nucleosides
  作者：Jiong J. Chen、Yuan Wei、John D. Williams、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257770500265646

  日期：2005.9.1

  A mild Knoevenagel coupling reaction between an indol-2-thione and a ribofuranose derivative was developed for the synthesis of 2-benzylthio-5,6-dichloro-3-(β-D-ribofuranosyl)indole (12). 3-(β-D-ribofuranosyl)-2,5,6-trichloroindole (16) was prepared from 12 in 4 steps. A Lewis acid-mediated glycosylation method was then developed to prepare the targeted 2-haloindole C-nucleoside 16 stereoselectively

  2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB), 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) 和 2-benzylthio- 5,6-二氯-1-(β-D-呋喃核糖基)苯并咪唑 (BTDCRB) 是苯并咪唑核苷，具有强大的选择性抗 HCMV 活性。多卤化吲哚 C-核苷制备为苯并咪唑核苷 TCRB 和 BDCRB 的 1-脱氮类似物。开发了 indol-2-thione 和 ribofuranose 衍生物之间的温和 Knoevenagel 偶联反应，用于合成 2-benzylthio-5,6-dichloro-3-(β-D-ribofuranosyl) indole (12)。3-(β-D-呋喃核糖基)-2,5,6-三氯吲哚 (16) 由 12
• Chemical investigations in the synthesis of O-serinyl aminoribosides
  作者：Maryon Ginisty、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.tetasy.2005.11.019

  日期：2006.1

  Glycosylation involving D-ribose derivatives and various N-protected tert-butyl L-serinates can be achieved efficiently by careful choice of the activation method at the anomeric position and of the Lewis acid promoter. The conditions described allow the major formation of the P-anomer required for further elaboration to liposidomycin and caprazamycin analogues. (c) 2005 Elsevier Ltd. All rights reserved.
• A versatile scaffold for a library of liposidomycins analogues: a crucial and potent glycosylation step
  作者：Christine Gravier-Pelletier、Maryon Ginisty、Yves Le Merrer

  DOI：10.1016/j.tetasy.2003.10.017

  日期：2004.1

  A key step for the synthesis of a diazepanone scaffold dedicated to a library of MraY inhibitors is described. It involves the O-glycosylation of a conveniently protected L-serine by a D-ribofuranose derivative. High yield and selectivity were obtained. (C) 2003 Elsevier Ltd. All rights reserved.
• Simple Synthesis of Aromatic β-C-Nucleosides via Coupling of Aryl Grignard Reagents with Sugar Fluorides
  作者：Masataka Yokoyama、Hirofumi Toyoshima、Miyuki Shimizu、Jun Mito、Hideo Togo

  DOI：10.1055/s-1998-4487

  日期：1998.4

  The perbenzylated d-ribofuranosyl fluoride is allowed to react with Grignard reagents of aromatic heterocycles such as thiophene, pyrrole, and indole in THF to afford the corresponding β-C-nucleosides in moderate yields. The present process can be also applied to perbenzylated d-glucopyranosyl fluoride and perbenzylated 2-deoxy-d-ribofuranosyl fluoride as sugar donors.

  过苄基化的d-核糖呋喃糖氟化物与芳香杂环如噻吩、吡咯和吲哚的格林纳试剂在THF中反应，得到相应的β-C-核苷，产率中等。该过程也可应用于过苄基化的d-葡萄糖吡喃糖氟化物和过苄基化的2-脱氧-d-核糖呋喃糖氟化物作为糖供体。
• A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using dast. Preparation of glycosyl fluorides.
  作者：Gary H. Posner、Stephen R. Haines

  DOI：10.1016/s0040-4039(00)98451-x

  日期：1985.1