4β-(1β)-1-(1',2'-dideoxy-1'-methoxycarbonylmethylidene-3',4';5',6'-di-O-isopropylidene-2-D-glucosyl)-4-(1α,2-epoxy-1β-methylethyl)-3β-methoxy-2-azetidinone | 503090-45-7

• 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: 4β-(1β)-1-(1',2'-dideoxy-1'-methoxycarbonylmethylidene-3',4';5',6'-di-O-isopropylidene-2-D-glucosyl)-4-(1α,2-epoxy-1β-methylethyl)-3β-methoxy-2-azetidinone
• 英文别名: methyl (E,4S)-4-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(2S,3S)-3-methoxy-2-[(2S)-2-methyloxiran-2-yl]-4-oxoazetidin-1-yl]but-2-enoate
• CAS: 503090-45-7
• 化学式: C₂₂H₃₃NO₉
• 分子量: 455.505
• InChiKey: BOVFPLIYBWUZLF-LPXBLHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4β-(1β)-1-(1',2'-dideoxy-1'-methoxycarbonylmethylidene-3',4';5',6'-di-O-isopropylidene-2-D-glucosyl)-4-(1α,2-epoxy-1β-methylethyl)-3β-methoxy-2-azetidinone 在 bis(cyclopentadienyl)titanium (III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以28%的产率得到β-[(1',2';3',4'-di-O-isopropylidene)-D-arabino-1',2',3',4'-tetrahydroxybutyl]-10β-methoxy-8α-methyl-6-oxa-5-oxo-3αH-9αH-tribactam
  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 、 碳酸氢钠 、 间氯过氧苯甲酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 101.0h， 生成 4β-(1β)-1-(1',2'-dideoxy-1'-methoxycarbonylmethylidene-3',4';5',6'-di-O-isopropylidene-2-D-glucosyl)-4-(1α,2-epoxy-1β-methylethyl)-3β-methoxy-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

文献信息

• Cyclization and rearrangement of 4-(2-methyloxiranyl)-β-lactams promoted by titanocene dichloride/Zn0
  作者：Josefa Anaya、Alfonso Fernández-Mateos、Manuel Grande、Justo Martiáñez、Gema Ruano、Ma Rosa Rubio-González

  DOI：10.1016/s0040-4020(02)01459-x

  日期：2003.1

  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.