N-((2R,3R,4R,5S,6R)-2-But-3-enyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide | 128902-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2R,3R,4R,5S,6R)-2-But-3-enyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide
• CAS: 128902-90-9
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: INNIWTKGZCVJQW-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.48
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.25
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-((2R,3R,4R,5S,6R)-2-But-3-enyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide 在 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 3,4-epoxybutyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-d-glucosamine derivatives

  摘要：

  The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00649-3
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 N-((2R,3R,4R,5S,6R)-2-But-3-enyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide
  参考文献：
  名称：

  Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-d-glucosamine derivatives

  摘要：

  The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00649-3