6-deoxy-6-formamido-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-formamido-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: N-[[(1S,2R,6R,8R,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-9-yl]methyl]formamide
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: ACWZQNURRDACGL-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-formamido-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到6-deoxy-1,2:3,5-di-O-isopropylidene-6-thioformamido-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and conformational properties of sugar amides and thioamides

  摘要：

  The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose at the primary carbon atom has been effected by thionation of the corresponding sugar amides. Formamides and thioformamides existed as a mixture of the Z (major) and E (minor) stereomers around the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the sole one detected in the cases of acetamides and thioacetamides.

  DOI：

  10.1016/s0957-4166(00)80381-x
• 作为产物：
  描述：

  6-amino-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose hydrochloride 、 甲乙酐 在 吡啶 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以95%的产率得到6-deoxy-6-formamido-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and conformational properties of sugar amides and thioamides

  摘要：

  The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose at the primary carbon atom has been effected by thionation of the corresponding sugar amides. Formamides and thioformamides existed as a mixture of the Z (major) and E (minor) stereomers around the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the sole one detected in the cases of acetamides and thioacetamides.

  DOI：

  10.1016/s0957-4166(00)80381-x

文献信息

• Synthesis and conformational properties of sugar amides and thioamides
  作者：Carmen Ortiz Mellet、Alberto Moreno Marín、José M. García Fernández、José Fuentes

  DOI：10.1016/s0957-4166(00)80381-x

  日期：1994.12

  The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose at the primary carbon atom has been effected by thionation of the corresponding sugar amides. Formamides and thioformamides existed as a mixture of the Z (major) and E (minor) stereomers around the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the sole one detected in the cases of acetamides and thioacetamides.