(E)-3-O-benzyl-6-deoxy-6-dimethylaminomethylene-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile | 887473-51-0

• 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: (E)-3-O-benzyl-6-deoxy-6-dimethylaminomethylene-1,2-O-isopropylidene-α-D-xylo-hept-5-ulofuranonitrile
• 英文别名: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminoethylene)-α-D-xylo-hept-5-ulofuranurononitrile；(E)-2-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbonyl]-3-(dimethylamino)prop-2-enenitrile
• CAS: 887473-51-0
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: OMWVKWLSKAESKJ-NGCXUTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-O-benzyl-6-deoxy-6-dimethylaminomethylene-1,2-O-isopropylidene-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94%的产率得到3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-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 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-3-O-benzyl-6-deoxy-6-dimethylaminomethylene-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

• Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues
  作者：Imran Ali Hashmi、Holger Feist、Manfred Michalik、Helmut Reinke、Klaus Peseke

  DOI：10.1515/znb-2006-0309

  日期：2006.3.1

  3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)-6-cyanopyrazolo[1,5-a]pyrimidine-3-carboxylates 4 and the ethyl 7-amino-6-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl)pyrazolo[1,5-a]pyrimidine- 3-carboxylates 5, respectively. Reaction of 1 with 2-benzimidazolylacetonitrile in the presence of sodium methanolate afforded 1-amino-2-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl) benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (6) and 1-amino-2-(3-deoxy-1,2-O-isopropylidene- α-D-glycero-pent-3-enofuranuronoyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (7).

  摘要：将3-O-苄基-6-去氧-1,2-O-异丙基亚甲基-6-(二甲氨亚甲基)-α-D-木糖-庚-5-烯-醛酸腈（1）分别与酰胺盐、S-甲基异硫脲硫酸盐和胍盐在碱的存在下反应，得到4-(3-O-苄基-1,2-O-异丙基-α-D-木糖-四氢呋喃-4-基)嘧啶-5-腈类化合物2和4-(1,2-O-异丙基-α-D-甘油-三烯呋喃-4-基)嘧啶-5-腈类化合物3。将1与乙基-5-氨基吡唑-4-羧酸酯处理，得到乙基-7-(3-O-苄基-1,2-O-异丙基-α-D-木糖-四氢呋喃-4-基)-6-氰基吡唑并[1,5-a]嘧啶-3-羧酸酯4和乙基-7-氨基-6-(3-O-苄基-1,2-O-异丙基-α-D-木糖-戊呋喃醛基)吡唑并[1,5-a]嘧啶-3-羧酸酯5。1与2-苯并咪唑基乙腈在甲醇钠存在下反应，得到1-氨基-2-(3-O-苄基-1,2-O-异丙基-α-D-木糖-戊呋喃醛基)苯并[4,5]咪唑并[1,2-a]吡啶-4-腈（6）和1-氨基-2-(3-去氧-1,2-O-异丙基-α-D-甘油-戊-3-烯呋喃醛基)苯并[4,5]咪唑并[1,2-a]吡啶-4-腈（7）。
• 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.