(4'S)-5-deoxy-3-O:5-C-[3'-(hydroxyimino)azetidin-2'-on-1',4'-diyl]-1,2-O-isopropylidene-α-D-xylofuranose | 333718-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'S)-5-deoxy-3-O:5-C-[3'-(hydroxyimino)azetidin-2'-on-1',4'-diyl]-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: (1S,2R,6R,8R,13S)-12-hydroxyimino-4,4-dimethyl-3,5,7,14-tetraoxa-10-azatetracyclo[6.6.0.02,6.010,13]tetradecan-11-one
• CAS: 333718-85-7
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: YQHVODADZVTMKR-YMNCXTEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (4'S)-5-deoxy-3-O:5-C-[3'-(hydroxyimino)azetidin-2'-on-1',4'-diyl]-1,2-O-isopropylidene-α-D-xylofuranose 在 platinum(IV) oxide 氢气 、 sodium acetate 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 26.0h， 以65%的产率得到(3'R,4'S)-3-O:5-C-[3'-(acetylamino)azetidin-2'-on-1',4'-diyl]-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Transformation of the 7-isopropylidene group in 5-dethia-5-oxacephams

  摘要：

  [2 + 2] Cycloaddition of CSI to 5-O-protected-3-0-allenyl-1,2-O-isopropylidene-alpha -D-xylofuranoses 8 and 9 gave respective p-lactams 10-13 having an exo-propylidene group, in moderate stereoselectivity. Compounds 10, 11 and tetracyclic cephams 14, 15 obtained from 10 and 11 or 12 and 13, were used as substrates for a variety of transformations leading to the introduction of isopropyl, hydroxyisopropyl, oxygen and nitrogen functions, or to the p-lactam carbonyl group. These reactions proceeded in high stereoselectivity with control of the absolute configuration of the cephams formed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01098-x
• 作为产物：
  描述：

  (4'S)-5-deoxy-3-O:5-C-[3'-hydroxy-3'-(1-hydroxy-1-methylethyl)azetidin-2'-on-1',4'-diyl]-1,2-O-isopropylidene-α-D-xylofuranose 在 盐酸羟胺 作用下， 以 乙酸乙酯 、 吡啶 为溶剂， 反应 74.5h， 以0.023 g的产率得到(4'S)-5-deoxy-3-O:5-C-[3'-(hydroxyimino)azetidin-2'-on-1',4'-diyl]-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Transformation of the 7-isopropylidene group in 5-dethia-5-oxacephams

  摘要：

  [2 + 2] Cycloaddition of CSI to 5-O-protected-3-0-allenyl-1,2-O-isopropylidene-alpha -D-xylofuranoses 8 and 9 gave respective p-lactams 10-13 having an exo-propylidene group, in moderate stereoselectivity. Compounds 10, 11 and tetracyclic cephams 14, 15 obtained from 10 and 11 or 12 and 13, were used as substrates for a variety of transformations leading to the introduction of isopropyl, hydroxyisopropyl, oxygen and nitrogen functions, or to the p-lactam carbonyl group. These reactions proceeded in high stereoselectivity with control of the absolute configuration of the cephams formed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01098-x