pent-4-enyl 3,5-di-O-benzyl-β-D-ribofuranoside | 1431370-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 3,5-di-O-benzyl-β-D-ribofuranoside
• 英文别名: (2R,3R,4S,5R)-2-pent-4-enoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 1431370-51-2
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: AHIFPGTXBNQEDV-MOUTVQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 3,5-di-O-benzyl-β-D-ribofuranoside 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 pent-4-enyl 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：

  卡培他滨杂质25 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 gold(III) chloride 、 乙酰溴 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 乙酰氯 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 pent-4-enyl 3,5-di-O-benzyl-β-D-ribofuranoside
  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

文献信息

• Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of <i>M. tuberculosis</i>
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/ol400931p

  日期：2013.5.17

  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.