2,3,5-tri-O-benzoyl-D-xylofuranosyl bromide | 55781-64-1

• 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-benzoyl-D-xylofuranosyl bromide
• 英文别名: Tri-O-benzoyl-D-xylofuranosylbromid；[(2R,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]methyl benzoate
• CAS: 55781-64-1
• 化学式: C₂₆H₂₁BrO₇
• 分子量: 525.353
• InChiKey: JRRCGOOKGUSEFK-VNYJYPEVSA-N

物化性质

• 沸点：
  611.4±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-D-xylofuranosyl bromide 在 2,6-二甲基吡啶 、 gold(III) chloride 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Gold(III)-Catalyzed Glycosidations for 1,2-trans and 1,2-cis Furanosides

  摘要：

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.

  DOI：

  10.1021/jo501052y
• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 在 吡啶 、 氢溴酸 、 溶剂黄146 、 乙酰氯 作用下， 反应 15.17h， 生成 2,3,5-tri-O-benzoyl-D-xylofuranosyl bromide
  参考文献：
  名称：

  由相应的甲基呋喃糖苷制备呋喃糖基正戊烯基原酸酯

  摘要：

  已经制备了四个戊呋喃糖酶的3，5-二-O-苯甲酰基正戊烯基原酸酯。在每种情况下，第一个关键中间体是甲基呋喃呋喃糖苷，并且根据Callam-Lowary的先例，描述了一种方便的制备方法，用于制备每种戊呋喃糖苷，从而优化了关键的α/β异头混合物的形成。将该混合物直接用于制备相应的过苯甲酰化的呋喃呋喃糖基溴化物，然后制备标题化合物。

  DOI：

  10.1021/jo1021376

文献信息

• An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction
  作者：Morwenna S. M. Pearson、Aélig Robin、Nathalie Bourgougnon、Jean Claude Meslin、David Deniaud

  DOI：10.1021/jo034709a

  日期：2003.10.1

  synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording

  我们在这里报告通过[4 + 2]环加成反应合成嘧啶核苷类似物的有效方法。这些化合物是通过收敛化学从糖基异硫氰酸酯3a-f（吡喃糖，呋喃糖和二糖）和二氮杂鎓盐5中获得的。实际上，由乙烯基硫酰胺4制备的碘化二戊戊二烯碘化物5是杂环合成中的有效中间体，并与异硫氰酸酯3a-f反应以高收率和完全的区域控制提供β-D-尿嘧啶类似物7a-f。所有化合物均通过IR，HRMS，13C和1H NMR（COSY和HMQC）充分表征。
• US4065616A
  申请人：——

  公开号：US4065616A

  公开（公告）日：1977-12-27
• Ready Preparation of Furanosyl<i>n</i>-Pentenyl Orthoesters from Corresponding Methyl Furanosides
  作者：Changalvala V. S. Ramamurty、Parimala Ganney、C. Srinivas Rao、Bert Fraser-Reid

  DOI：10.1021/jo1021376

  日期：2011.4.1

  The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam−Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding

  已经制备了四个戊呋喃糖酶的3，5-二-O-苯甲酰基正戊烯基原酸酯。在每种情况下，第一个关键中间体是甲基呋喃呋喃糖苷，并且根据Callam-Lowary的先例，描述了一种方便的制备方法，用于制备每种戊呋喃糖苷，从而优化了关键的α/β异头混合物的形成。将该混合物直接用于制备相应的过苯甲酰化的呋喃呋喃糖基溴化物，然后制备标题化合物。
• Gold(III)-Catalyzed Glycosidations for 1,2-<i>trans</i> and 1,2-<i>cis</i> Furanosides
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/jo501052y

  日期：2014.8.15

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.