(4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-azetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose | 166887-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-azetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose
• 英文别名: (4'R) 5-amino-5-deoxy-1,2-O-isopropylidene-3-O:5-N-(azetidin-2'-onyl-4')-α-D-xylofuranose；(1S,2R,6R,8R,13R)-4,4-dimethyl-3,5,7,14-tetraoxa-10-azatetracyclo[6.6.0.02,6.010,13]tetradecan-11-one
• CAS: 166887-23-6
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: LHGNCEAFUXUYKW-SVFDORGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  对硝基苯甲醛 、 (4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-azetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以53%的产率得到(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-nitrobenzyl)-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'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-trimethylsilylazetidin-2'-on-4'-yl)-5-O-trityl-α-D-xylofuranose 在 甲酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.25h， 生成 (4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-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

文献信息

• Asymmetric induction in [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinyl-glycofuranoses
  作者：Zbigniew Kałuża、Bartłomiej Furman、Madhumeeta Patel、Marek Chmielewski

  DOI：10.1016/s0957-4166(00)86293-x

  日期：1994.11

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinylglycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.
• Stereoselective Solid-Phase Synthesis of -Lactams—A Novel Cyclization/Cleavage Step towards 1-Oxacephams
  作者：Bartłomiej Furman、René Thürmer、Zbigniew Kałuża、Robert Łysek、Wolfgang Voelter、Marek Chmielewski

  DOI：10.1002/(sici)1521-3773(19990419)38:8<1121::aid-anie1121>3.0.co;2-d

  日期：1999.4.19

  Despite the antibiotic activity and the attractiveness of β-lactams, the solid-phase synthesis of this class of compounds has been barely reported. Now the diastereoselective synthesis of the 1-oxacepham 2 from the resin-bound β-lactam derivative 1 has been achieved in five steps. The synthesis of 2 and other 1-oxacephams is attractive because all the reaction steps proceed in high yield, the purity of the product is high, and the reaction sequence is simple.
• [2+2]cycloaddition of chlorosulfonyl isocyanate to (Z) 3-O-(2′-silylvinyl) ethers of 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose
  作者：R Łysek、Z Kałuża、B Furman、M Chmielewski

  DOI：10.1016/s0040-4020(98)00857-6

  日期：1998.11

  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.