(-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide | 398460-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide
• 英文别名: (2S,3S,6S)-3-hydroxy-N-phenylmethoxy-6-(2,2,2-trichloroethoxy)-3,6-dihydro-2H-pyran-2-carboxamide
• CAS: 398460-13-4
• 化学式: C₁₅H₁₆Cl₃NO₅
• 分子量: 396.655
• InChiKey: BMCGQNYANWBKFB-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以72%的产率得到(-)-(1S,3S,6R)-7-benzyloxy-2-O-oxa-8-oxo-3-O-(2,2,2-trichloroethyl)-7-azabicyclo[4.2.0]oct-4-ene
  参考文献：
  名称：

  Conversion of Glucuronic Acid Glycosides to Novel Bicyclic β-Lactams

  摘要：

  GRAPHICSMethodology for the conversion of glucuronic acid glycosides to novel bicyclic beta-lactams is reported. Using this strategy, we prepared two novel templates suitable for use in combinatorial chemistry strategies for the construction of a number of interesting beta-lactam motifs. Key features of this strategy include a diastereoselective Ferrier reaction of a glucuronic acid glucal, selective beta-lactam ring formation using a cyclic allylic alcohol, and a chemoselective benzylic oxidation.

  DOI：

  10.1021/ol017026v
• 作为产物：
  描述：

  (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯 在 三氟化硼乙醚 、 potassium trimethylsilonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide
  参考文献：
  名称：

  Conversion of Glucuronic Acid Glycosides to Novel Bicyclic β-Lactams

  摘要：

  GRAPHICSMethodology for the conversion of glucuronic acid glycosides to novel bicyclic beta-lactams is reported. Using this strategy, we prepared two novel templates suitable for use in combinatorial chemistry strategies for the construction of a number of interesting beta-lactam motifs. Key features of this strategy include a diastereoselective Ferrier reaction of a glucuronic acid glucal, selective beta-lactam ring formation using a cyclic allylic alcohol, and a chemoselective benzylic oxidation.

  DOI：

  10.1021/ol017026v

文献信息

• Conversion of Glucuronic Acid Glycosides to Novel Bicyclic <i>β</i>-Lactams
  作者：Timothy B. Durham、Marvin J. Miller

  DOI：10.1021/ol017026v

  日期：2002.1.1

  GRAPHICSMethodology for the conversion of glucuronic acid glycosides to novel bicyclic beta-lactams is reported. Using this strategy, we prepared two novel templates suitable for use in combinatorial chemistry strategies for the construction of a number of interesting beta-lactam motifs. Key features of this strategy include a diastereoselective Ferrier reaction of a glucuronic acid glucal, selective beta-lactam ring formation using a cyclic allylic alcohol, and a chemoselective benzylic oxidation.