(3'S,4'S)-3-O-(3'-isopropylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose | 333718-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S,4'S)-3-O-(3'-isopropylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: (3S,4S)-4-[[(3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3-propan-2-ylazetidin-2-one
• CAS: 333718-68-6
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: SYDAIPAFCGFNDS-ZAPDOIONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3'S,4'S)-3-O-(3'-isopropylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 作用下， 反应 12.0h， 生成 (3'S,4'S)-5-deoxy-3-O:5-C-(3'-isopropylazetidin-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
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)azetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose 在 sodium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.42h， 以48%的产率得到(3'R,4'R)-3-O-(3'-isopropylazetidin-2'-on-4'-yl)-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