(3'S, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose | 218146-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS: 218146-95-3
• 化学式: C₁₇H₃₁NO₆Si
• 分子量: 373.522
• InChiKey: KTHODVDIUKNQLI-JCJKHTMNSA-N

物化性质

• 沸点：
  489.570±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.172±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

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：

  (3'S, 4'R)-3-O-(3'-t-butyldimethylsilylazetidin-2'-on-4'-yl)-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 57.0h， 生成 (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-acetoxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-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：

  (Z)-3-O-(2'-t-butyldilmethylsilylvinyl)-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 在 甲酸 、 sodium carbonate 、 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 (3'S, 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