2-azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilyl-7-O-trityl-D-glycero-D-allo-heptonamide | 635678-99-8

• 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: 2-azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilyl-7-O-trityl-D-glycero-D-allo-heptonamide
• 英文别名: (2R,3S)-2-azido-N,N-diethyl-3-[(4R,5R)-5-[(1R)-1-hydroxy-2-trityloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-tri(propan-2-yl)silyloxypropanamide
• CAS: 635678-99-8
• 化学式: C₄₂H₆₀N₄O₆Si
• 分子量: 745.047
• InChiKey: IMTZDSZHGYGFFR-VRSORNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.98
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilyl-7-O-trityl-D-glycero-D-allo-heptonamide 在 sodium methylate 、 三苯基膦 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 氯仿 为溶剂， 生成 (3aR,4R,6R,7S,7aR)-4-Hydroxymethyl-2,2-dimethyl-7-triisopropylsilanyloxy-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid diethylamide
  参考文献：
  名称：

  来自α，β-环氧酰胺的氨基糖。第1部分：羟基化哌啶衍生物的合成方法

  摘要：

  描述了一种从手性环氧酰胺开始的合成亚氨基糖的新途径。可以将单一的前体，即由6 - O-三苯甲基-2,3- O-异亚丙基-d-核糖和硫内酰胺制得的α，β-环氧酰胺转化成不同的亚氨基糖的策略。区域选择性环氧化物开口和立体定向分子内位移的组合。

  DOI：

  10.1016/j.tetlet.2003.09.116
• 作为产物：
  描述：

  三异丙基硅基三氟甲磺酸酯 、 2-azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-D-glycero-D-allo-heptonamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以60%的产率得到2-azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilyl-7-O-trityl-D-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

• Iminosugars from α,β-epoxyamides. Part 1: Synthetic approach to hydroxylated piperidine derivatives
  作者：M.Soledad Pino-González、Carmen Assiego、F.Jorge López-Herrera

  DOI：10.1016/j.tetlet.2003.09.116

  日期：2003.11

  A new synthetic route towards iminosugars starting from chiral epoxyamides is described. The strategy, by which a single precursor, the α,β-epoxyamide obtained from 6-O-trityl-2,3-O-isopropylidene-d-ribose and a sulphur ylide, can be transformed into different iminosugars, is based on the combination of a regioselective epoxide opening and stereospecific intramolecular displacements.

  描述了一种从手性环氧酰胺开始的合成亚氨基糖的新途径。可以将单一的前体，即由6 - O-三苯甲基-2,3- O-异亚丙基-d-核糖和硫内酰胺制得的α，β-环氧酰胺转化成不同的亚氨基糖的策略。区域选择性环氧化物开口和立体定向分子内位移的组合。
• 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.