(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(tert-butoxy)dihydrofuran-3(2H)-one | 1431370-70-5

• 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: (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(tert-butoxy)dihydrofuran-3(2H)-one
• CAS: 1431370-70-5
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: JLGUVDRNGXYXDC-FCEUIQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(tert-butoxy)dihydrofuran-3(2H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 tert-butyl 3,5-di-O-benzyl-β-D-arabinofuranoside
  参考文献：
  名称：

  Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

  摘要：

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

  DOI：

  10.1021/ol400931p
• 作为产物：
  描述：

  tert-butyl 2-O-benzoyl-3,5-di-O-benzyl-β-D-ribofuranoside 在 sodium methylate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(tert-butoxy)dihydrofuran-3(2H)-one
  参考文献：
  名称：

  Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

  摘要：

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

  DOI：

  10.1021/ol400931p