(3'S, 4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilylazetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose | 218146-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: (3'S, 4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilylazetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose
• 英文别名: (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilyl-azetidin-2'-on-1',4'-diyl)-α-D-xylofuranose；(1S,2R,6R,8R,12S,13R)-12-[tert-butyl(dimethyl)silyl]-4,4-dimethyl-3,5,7,14-tetraoxa-10-azatetracyclo[6.6.0.02,6.010,13]tetradecan-11-one
• CAS: 218146-99-7
• 化学式: C₁₇H₂₉NO₅Si
• 分子量: 355.506
• InChiKey: HJUJTJXZQHDIPD-JCJKHTMNSA-N

物化性质

• 沸点：
  431.836±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.179±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3'S, 4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilylazetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 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：

  3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 甲酸 、 四丁基溴化铵 、 氢气 、 sodium carbonate 、 potassium carbonate 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 (3'S, 4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilylazetidin-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