N-[(3R,4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-thioacetamide | 805245-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(3R,4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-thioacetamide
• CAS: 805245-15-2
• 化学式: C₈H₁₃NO₅S
• 分子量: 235.261
• InChiKey: UVKYWDIKPGKJHE-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.07
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N-[(3R,4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-thioacetamide 在 吡啶 作用下， 以54%的产率得到Acetic acid 2-[4-acetylamino-5-oxo-5H-furan-(2E)-ylidene]-ethyl ester
  参考文献：
  名称：

  A fused GalNAc-thiazole from a singular and unanticipated fragmentation

  摘要：

  Attempted O-desilylation of an elaborated GalNAc-thiazoline t-butyl ester gave rise instead to a GalNAc-thiazole wherein the two-carbon acetate side chain has been severed by a process heretofore undescribed. The corresponding ether ester rearranged to a C-furanoside by a quite different pathway. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.091
• 作为产物：
  描述：

  2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone 在 Ra-Ni 劳森试剂 、 n-BuNF*H₂O 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 N-[(3R,4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-thioacetamide
  参考文献：
  名称：

  A fused GalNAc-thiazole from a singular and unanticipated fragmentation

  摘要：

  Attempted O-desilylation of an elaborated GalNAc-thiazoline t-butyl ester gave rise instead to a GalNAc-thiazole wherein the two-carbon acetate side chain has been severed by a process heretofore undescribed. The corresponding ether ester rearranged to a C-furanoside by a quite different pathway. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.091