3,6-anhydro-2-azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-L-glycero-D-allo-heptonamide | 1038433-22-5

• 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: 3,6-anhydro-2-azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-L-glycero-D-allo-heptonamide
• 英文别名: (2R)-2-[(3aS,4S,6S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-azido-N,N-diethylacetamide
• CAS: 1038433-22-5
• 化学式: C₃₃H₃₈N₄O₅
• 分子量: 570.689
• InChiKey: RUXKPCWHUMBHFL-NAGJOQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Methanesulfonic acid (R)-1-[(4S,5S)-5-((2R,3S)-3-diethylcarbamoyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-trityloxy-ethyl ester 在 sodium azide 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以76%的产率得到3,6-anhydro-2-azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-L-glycero-D-allo-heptonamide
  参考文献：
  名称：

  Studies on reactivity of azidoamides, intermediates in the synthesis of tetrahydroxypipecolic acid derivatives

  摘要：

  Azido group reduction was observed by the treatment of a 2-azido-3-triisopropylsilyloxy heptonamide derivative with NaI in DMSO. The process allowed us to obtain a tetrahydroxypipecolic acid amide derivative. The same azido amide was treated with LiCl in DMSO, but desilylation occurred to give 3,6-anhydro-2-azido heptonamide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.018

文献信息

• Studies on reactivity of azidoamides, intermediates in the synthesis of tetrahydroxypipecolic acid derivatives
  作者：M.-Soledad Pino-González、Carmen Assiego、Noé Oña

  DOI：10.1016/j.tetasy.2008.03.018

  日期：2008.5

  Azido group reduction was observed by the treatment of a 2-azido-3-triisopropylsilyloxy heptonamide derivative with NaI in DMSO. The process allowed us to obtain a tetrahydroxypipecolic acid amide derivative. The same azido amide was treated with LiCl in DMSO, but desilylation occurred to give 3,6-anhydro-2-azido heptonamide. (C) 2008 Elsevier Ltd. All rights reserved.