(3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-butan-1-one | 436148-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-butan-1-one
• 英文别名: (3R,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methylphenyl)-3,4-bis(phenylmethoxy)butan-1-one
• CAS: 436148-74-2
• 化学式: C₃₀H₃₄O₅
• 分子量: 474.597
• InChiKey: DBNHWCOHWPEAQO-NLDZOOGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-butan-1-one 在 硫酸 、 水 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 2-((2R,3R,4R)-3-Benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-1-p-tolyl-ethanone 、 2-((2S,3R,4R)-3-Benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-1-p-tolyl-ethanone
  参考文献：
  名称：

  Umpolung Strategy for the Synthesis of 2-Deoxy-C-aryl Glycosides:  A Serendipitous, Efficient Route for C-Furanoside Analogues

  摘要：

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.

  DOI：

  10.1021/ol025794w
• 作为产物：
  描述：

  (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 、 sodium hydride 、 碳酸氢钠 、 copper(II) sulfate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 36.25h， 生成 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-butan-1-one
  参考文献：
  名称：

  Umpolung Strategy for the Synthesis of 2-Deoxy-C-aryl Glycosides:  A Serendipitous, Efficient Route for C-Furanoside Analogues

  摘要：

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.

  DOI：

  10.1021/ol025794w

文献信息

• Umpolung Strategy for the Synthesis of 2-Deoxy-<i>C</i>-aryl Glycosides:  A Serendipitous, Efficient Route for <i>C</i>-Furanoside Analogues
  作者：S. Vijayasaradhi、Indrapal Singh Aidhen

  DOI：10.1021/ol025794w

  日期：2002.5.1

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.