3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose | 218146-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-6-ethynoxy-2,2-dimethyl-5-(trityloxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 218146-76-0
• 化学式: C₂₉H₂₈O₅
• 分子量: 456.538
• InChiKey: IEKBKSIDHZZXQV-HVWQDESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 氢气 、 sodium carbonate 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.0h， 生成 (3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-trimethylsilylazetidin-2'-on-4'-yl)-5-O-trityl-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：

  三氯乙烯 、 1,2-O-(异丙亚基)-5-O-(三苯基甲基)-alpha-D-呋喃木糖 生成 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-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