2,3-di-O-benzoyl-4,5-dideoxy-D-threo-pent-4-enose | 848862-07-7

• 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-di-O-benzoyl-4,5-dideoxy-D-threo-pent-4-enose
• 英文别名: [(3R,4S)-4-benzoyloxy-5-oxopent-1-en-3-yl] benzoate
• CAS: 848862-07-7
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: IQHIGIQVIBRVCN-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzoyl-4,5-dideoxy-D-threo-pent-4-enose 在 吡啶 、 盐酸 、 盐酸羟胺 、 methyl orange 、 sodium cyanoborohydride 、 sodium sulfate 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 (3R,4S,5S)-3,4-dibenzoyloxy-8-oxa-1-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis of a trihydroxylated azepane from d-arabinose by way of an intramolecular alkene nitrone cycloaddition

  摘要：

  The synthesis of 1,6-imino-1,5,6-trideoxy-(L)-xylo-hexitol, a trihydroxylated azepane, from (D)-arabinose was achieved by way of an intramolecular alkene nitrone cycloaddition. The final product as well as its bicyclic precursor, (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane, were evaluated as glycosidase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.041
• 作为产物：
  描述：

  苯甲酰氯 、 methyl 5-deoxy-5-iodo-D-arabinofuranoside 在 cyanocobalamin 、 锌 作用下， 以57%的产率得到2,3-di-O-benzoyl-4,5-dideoxy-D-threo-pent-4-enose
  参考文献：
  名称：

  Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides

  摘要：

  The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to alpha-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.079

文献信息

• Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses
  作者：Gaëlle Fourrière、Jérôme Lalot、Nathalie Van Hijfte、Jean-Charles Quirion、Eric Leclerc

  DOI：10.1016/j.tetlet.2009.09.170

  日期：2009.12

  The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes followed by a radical cyclization, and provides a secure strategy for a future synthesis of pentofuranoses and nucleoside analogues.

  描述了5-脱氧戊呋喃糖酶的二氟化碳环类似物的合成。该序列涉及将PhSeCF 2 TMS添加到碳水化合物衍生的醛中，然后进行自由基环化，并为将来合成戊呋喃糖酶和核苷类似物提供了安全的策略。