(3β,4β)-1-(1',2'-dideoxy-1',1'-diethylthio-3',4';5',6'-di-O-isopropylidene-2'-D-glucosyl)-3-methoxy-4-(1-methylethenyl)-2-azetidinone | 503090-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3β,4β)-1-(1',2'-dideoxy-1',1'-diethylthio-3',4';5',6'-di-O-isopropylidene-2'-D-glucosyl)-3-methoxy-4-(1-methylethenyl)-2-azetidinone
• CAS: 503090-42-4
• 化学式: C₂₃H₃₉NO₆S₂
• 分子量: 489.698
• InChiKey: OPSXWBNUEDJUPW-UPGMHYFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3β,4β)-1-(1',2'-dideoxy-1',1'-diethylthio-3',4';5',6'-di-O-isopropylidene-2'-D-glucosyl)-3-methoxy-4-(1-methylethenyl)-2-azetidinone 在 碳酸氢钠 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 生成 (R)-((2R,3S)-2-Isopropenyl-3-methoxy-4-oxo-azetidin-1-yl)-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde
  参考文献：
  名称：

  Cyclization and rearrangement of 4-(2-methyloxiranyl)-β-lactams promoted by titanocene dichloride/Zn0

  摘要：

  Enantiopure epoxyalkene-2-azetidinones derived from D-glucosamine by Staudinger reaction gave on treatment for 2 h with titanoncene (III) monochloride generated in situ, bicyclic and tricyclic beta-lactams with high regio and stereo-selectivity but with low conversion. For extended reaction times (15-22 h) a rearranged five-membered ring imide was the main reaction product together with the tribactam. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01459-x
• 作为产物：
  描述：

  3,4:5,6-di-O-isopropylidene-1,1-bis-ethylsulfanyl-D-glucosamine 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 84.0h， 生成 (3β,4β)-1-(1',2'-dideoxy-1',1'-diethylthio-3',4';5',6'-di-O-isopropylidene-2'-D-glucosyl)-3-methoxy-4-(1-methylethenyl)-2-azetidinone
  参考文献：
  名称：

  Cyclization and rearrangement of 4-(2-methyloxiranyl)-β-lactams promoted by titanocene dichloride/Zn0

  摘要：

  Enantiopure epoxyalkene-2-azetidinones derived from D-glucosamine by Staudinger reaction gave on treatment for 2 h with titanoncene (III) monochloride generated in situ, bicyclic and tricyclic beta-lactams with high regio and stereo-selectivity but with low conversion. For extended reaction times (15-22 h) a rearranged five-membered ring imide was the main reaction product together with the tribactam. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01459-x