3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-α-D-xylo-hept-5-ulofuranonitrile | 887473-54-3

• 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-6-[bis(methylsulfanyl)methylene]-α-D-xylo-hept-5-ulofuranonitrile
• 英文别名: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-α-D-xylo-hept-5-ulofuranuronitrile；2-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbonyl]-3,3-bis(methylsulfanyl)prop-2-enenitrile
• CAS: 887473-54-3
• 化学式: C₂₀H₂₃NO₅S₂
• 分子量: 421.538
• InChiKey: FJDUODODBWFNQJ-XMTFNYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-α-D-xylo-hept-5-ulofuranonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以87%的产率得到3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-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 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-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’ Pyrimidine and Pyrazolo[1,5-<i>a</i>]pyrimidine-<i>C</i>-Nucleoside Analogues from Push-Pull Functionalized α-<scp>d</scp>-<i>xylo</i>-Hept-5-ulofuranurononitrile
  作者：Imran Hashmi、Firdous Ali、Holger Feist、Manfred Michalik、Helmut Reinke、Klaus Peseke

  DOI：10.1055/s-2007-983879

  日期：2007.9

  3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(meth­ylsulfanyl)methylene]-α-d-xylo-hept-5-ulofuranurononitrile (1) was reacted with acetamidinium chloride, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of triethylamine to furnish the 2-substituted 4-(3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrimidine-5-carbonitriles 2a-c. Treatment of 1 with different 5-aminopyrazole-4-carboxylic acid derivatives yielded the 8-(3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrazolo[1,5-a]pyrimidine-3,7-dicarboxylic acid derivatives 3a-c.

  3-O-苄基-6-脱氧-1,2-O-异亚丙基-6-[双(甲硫基)亚甲基]-α-d-吡喃木型庚-5-呋喃脲腈（1）在与三乙胺存在下分别与乙酰胺脒盐酸盐、S-甲基异硫脲硫酸盐和胍盐酸盐反应，得到2-取代的4-(3-O-苄基-1,2-O-异亚丙基-α-d-吡喃木型四氢呋喃-4-基)-6-甲硫基嘧啶-5-腈2a-c。将1与不同的5-氨基吡唑-4-羧酸衍生物反应，得到8-(3-O-苄基-1,2-O-异亚丙基-α-d-吡喃木型四氢呋喃-4-基)-6-甲硫基吡唑并[1,5-a]嘧啶-3,7-二羧酸衍生物3a-c。