(3'R, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose | 218146-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'R, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS: 218146-96-4
• 化学式: C₁₇H₃₁NO₆Si
• 分子量: 373.522
• InChiKey: KTHODVDIUKNQLI-RIMRTXSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 (3'R, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose 以65%的产率得到(3'R, 4'R)-1,2-O-isopropylidene-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-5-O-tosyl-α-D-xylofuranose
  参考文献：
  名称：

  [2+2]cycloaddition of chlorosulfonyl isocyanate to (Z) 3-O-(2′-silylvinyl) ethers of 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

  摘要：

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-2'-silylvinyl)-5-O-trityl-alpha-D-xylofuranose proceeds with high steroselectivity in a good yield to afford the corresponding azetidin-2-ones with (R) configuration at the newly formed stereogenic center. The bulky t-butyl-dimethyisilyl substituent causes partial epimerization at C-3' carbon atom of the azetidin-2-one ring. Intramolecular alkylation of the nitrogen atom by the terminal carbon of the sugar chain gives 1-oxacephams; basic conditions of cyclization cause desilylation or partial desilylation of products. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00857-6
• 作为产物：
  描述：

  1,2-O-(异丙亚基)-5-O-(三苯基甲基)-alpha-D-呋喃木糖 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 甲酸 、 氢气 、 sodium carbonate 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 4.0h， 生成 (3'R, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  [2+2]cycloaddition of chlorosulfonyl isocyanate to (Z) 3-O-(2′-silylvinyl) ethers of 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

  摘要：

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-2'-silylvinyl)-5-O-trityl-alpha-D-xylofuranose proceeds with high steroselectivity in a good yield to afford the corresponding azetidin-2-ones with (R) configuration at the newly formed stereogenic center. The bulky t-butyl-dimethyisilyl substituent causes partial epimerization at C-3' carbon atom of the azetidin-2-one ring. Intramolecular alkylation of the nitrogen atom by the terminal carbon of the sugar chain gives 1-oxacephams; basic conditions of cyclization cause desilylation or partial desilylation of products. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00857-6