isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-3-[bis(methylthio)methylene]-4-thio-α-D-threo-hexopyranosid-2-ulose | 797790-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-3-[bis(methylthio)methylene]-4-thio-α-D-threo-hexopyranosid-2-ulose
• 英文别名: isopropyl 6-O-acetyl-3-[bis(methylthio)methylene]-3-deoxy-4-S-ethyl-4-thio-α-D-threo-hexopyranosid-2-ulose；[(2R,3R,6S)-4-[bis(methylsulfanyl)methylidene]-3-ethylsulfanyl-5-oxo-6-propan-2-yloxyoxan-2-yl]methyl acetate
• CAS: 797790-21-7
• 化学式: C₁₆H₂₆O₅S₃
• 分子量: 394.577
• InChiKey: JKPJLBJIBZGXTI-UGFHNGPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-3-[bis(methylthio)methylene]-4-thio-α-D-threo-hexopyranosid-2-ulose 在 sodium tetrahydroborate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.34h， 生成 (4R,5R,7S)-4-ethylsulfanyl-7-isopropoxy-1,4,5,7-tetrahydropyrano[3,4-c]pyrazol-5-ylmethyl acetate
  参考文献：
  名称：

  Synthesis of Novel Anellated Pyranosides as Precursors of C‐Nucleoside Analogues Using Isopropyl 6‐O‐Acetyl‐3‐deoxy‐4‐S‐ethyl‐4‐thio‐α‐D‐threo‐hexopyranosid‐2‐ulose

  摘要：

  Isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-4-thio-alpha-D-threo-hexopyranosid-2-ulose (3) was converted to the corresponding 3-[bis(methylthio)methylene] derivative 4 with a push-pull activated C-C double bond. Treatment of 4 with hydrazine and methylhydrazine afforded the pyrano[3,4-c]pyrazol-5-ylmethyl acetates 5a and 5b, respectively. Desulfurization of compound 4 with sodium boron hydride yielded the 3-[(methylthio)methylene]hexopyranosid-2-ulose 7. Compound 7 was reacted with amines to furnish 3-aminomethylene-hexopyranosid-2-uloses 8, 9. Reaction of 7 with hydrazine hydrate, hydrazines, hydroxylamine, and benzamidine afforded the pyrazolo, isoxazalo, and pyrimido anellated pyranosides (10-13).

  DOI：

  10.1081/car-200035744
• 作为产物：
  描述：

  二硫化碳 、 isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-4-thio-α-D-threo-hexopyranosid-2-ulose 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-3-[bis(methylthio)methylene]-4-thio-α-D-threo-hexopyranosid-2-ulose
  参考文献：
  名称：

  Synthesis of Novel Anellated Pyranosides as Precursors of C‐Nucleoside Analogues Using Isopropyl 6‐O‐Acetyl‐3‐deoxy‐4‐S‐ethyl‐4‐thio‐α‐D‐threo‐hexopyranosid‐2‐ulose

  摘要：

  Isopropyl 6-O-acetyl-3-deoxy-4-S-ethyl-4-thio-alpha-D-threo-hexopyranosid-2-ulose (3) was converted to the corresponding 3-[bis(methylthio)methylene] derivative 4 with a push-pull activated C-C double bond. Treatment of 4 with hydrazine and methylhydrazine afforded the pyrano[3,4-c]pyrazol-5-ylmethyl acetates 5a and 5b, respectively. Desulfurization of compound 4 with sodium boron hydride yielded the 3-[(methylthio)methylene]hexopyranosid-2-ulose 7. Compound 7 was reacted with amines to furnish 3-aminomethylene-hexopyranosid-2-uloses 8, 9. Reaction of 7 with hydrazine hydrate, hydrazines, hydroxylamine, and benzamidine afforded the pyrazolo, isoxazalo, and pyrimido anellated pyranosides (10-13).

  DOI：

  10.1081/car-200035744