(3R,4S)-1-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one | 436148-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (3R,4S)-1-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one
• 英文别名: (3R,4S)-1-(1,3-benzodioxol-5-yl)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-bis(phenylmethoxy)butan-1-one
• CAS: 436148-76-4
• 化学式: C₃₀H₃₂O₇
• 分子量: 504.58
• InChiKey: GIWVOIXSPFCRBQ-NLDZOOGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one 在 硫酸 、 水 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 1-Benzo[1,3]dioxol-5-yl-2-((2R,3R,4R)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-ethanone 、 1-Benzo[1,3]dioxol-5-yl-2-((2S,3R,4R)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-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：

  (4R,5S)-2-Benzo[1,3]dioxol-5-yl-4,5-bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-pentanenitrile 在 水 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (3R,4S)-1-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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