3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile | 887473-59-8

• 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: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile
• 英文别名: 3-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-oxopropanenitrile
• CAS: 887473-59-8
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: ALGNJRHROFVMNH-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.25h， 生成 3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-1-methyl-5-methylsulfanyl-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis of “Reversed” Pyrazole‐C‐nucleoside Precursors from Push‐pull Activated Monosaccharide Derivatives

  摘要：

  3- O -Benzyl-6-deoxy-1,2- O -isopropylidene-alpha-d- xylo -hept-5- ulofuranurononitrile (1) was reacted with N , N -dimethylformamide dimethylacetal in tetrahydrofuran to furnish the ( E )-3- O -benzyl-6-deoxy-6-dimethylaminomethylene-1,2- O -isopropylidene-a-d- xylo -hept-5-ulofuranurononitrile (2) as a major product. Furthermore, treatment of compound 1 with carbon disulphide and methyl iodide under basic conditions afforded 3- O -benzyl-6-deoxy-1,2- O -isopropylidene-6-[bis(methylsulfanyl)methylene]-alpha-d- xylo -hept-5-ulofuranurononitrile (6). Reaction of 2 and 6 with hydrazines yielded the "reversed pyrazole- C -nucleoside analogs 4, 5a, 5b, 7, 8, and 9, respectively.

  DOI：

  10.1080/07328300500471770
• 作为产物：
  描述：

  3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptfuranonitrile 在 3 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65.7%的产率得到3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile
  参考文献：
  名称：

  Synthesis of “Reversed” Pyrazole‐C‐nucleoside Precursors from Push‐pull Activated Monosaccharide Derivatives

  摘要：

  3- O -Benzyl-6-deoxy-1,2- O -isopropylidene-alpha-d- xylo -hept-5- ulofuranurononitrile (1) was reacted with N , N -dimethylformamide dimethylacetal in tetrahydrofuran to furnish the ( E )-3- O -benzyl-6-deoxy-6-dimethylaminomethylene-1,2- O -isopropylidene-a-d- xylo -hept-5-ulofuranurononitrile (2) as a major product. Furthermore, treatment of compound 1 with carbon disulphide and methyl iodide under basic conditions afforded 3- O -benzyl-6-deoxy-1,2- O -isopropylidene-6-[bis(methylsulfanyl)methylene]-alpha-d- xylo -hept-5-ulofuranurononitrile (6). Reaction of 2 and 6 with hydrazines yielded the "reversed pyrazole- C -nucleoside analogs 4, 5a, 5b, 7, 8, and 9, respectively.

  DOI：

  10.1080/07328300500471770

文献信息

• Synthesis of “Reversed” Pyrazole‐<i>C</i>‐nucleoside Precursors from Push‐pull Activated Monosaccharide Derivatives
  作者：Imran Ali Hashmi、Holger Feist、Manfred Michalik、Helmut Reinke、Klaus Peseke

  DOI：10.1080/07328300500471770

  日期：2006.1.1

  3- O -Benzyl-6-deoxy-1,2- O -isopropylidene-alpha-d- xylo -hept-5- ulofuranurononitrile (1) was reacted with N , N -dimethylformamide dimethylacetal in tetrahydrofuran to furnish the ( E )-3- O -benzyl-6-deoxy-6-dimethylaminomethylene-1,2- O -isopropylidene-a-d- xylo -hept-5-ulofuranurononitrile (2) as a major product. Furthermore, treatment of compound 1 with carbon disulphide and methyl iodide under basic conditions afforded 3- O -benzyl-6-deoxy-1,2- O -isopropylidene-6-[bis(methylsulfanyl)methylene]-alpha-d- xylo -hept-5-ulofuranurononitrile (6). Reaction of 2 and 6 with hydrazines yielded the "reversed pyrazole- C -nucleoside analogs 4, 5a, 5b, 7, 8, and 9, respectively.