[(1R)-1-[(4S,5R)-5-[(1S,2R)-2-azido-3-(diethylamino)-3-oxo-1-tri(propan-2-yl)silyloxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trityloxyethyl] chloromethanesulfonate | 934271-05-3

• 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: [(1R)-1-[(4S,5R)-5-[(1S,2R)-2-azido-3-(diethylamino)-3-oxo-1-tri(propan-2-yl)silyloxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trityloxyethyl] chloromethanesulfonate
• CAS: 934271-05-3
• 化学式: C₄₃H₆₁ClN₄O₈SSi
• 分子量: 857.584
• InChiKey: ZPRZGIDUHHWRFF-PFWGIBHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R)-1-[(4S,5R)-5-[(1S,2R)-2-azido-3-(diethylamino)-3-oxo-1-tri(propan-2-yl)silyloxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trityloxyethyl] chloromethanesulfonate 在 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以75%的产率得到N,N-diethyl-2,6-dideoxy-2,6-imino-4,5-O-isopropylidene-3-O-triisopropylsilyl-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
• 作为产物：
  描述：

  氯甲磺酰氯 、 2-azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilyl-7-O-trityl-D-glycero-D-allo-heptonamide 在 吡啶 作用下， 反应 0.75h， 以100%的产率得到[(1R)-1-[(4S,5R)-5-[(1S,2R)-2-azido-3-(diethylamino)-3-oxo-1-tri(propan-2-yl)silyloxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trityloxyethyl] chloromethanesulfonate
  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.