2,2,2-trichloroethyl ((2R,4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-(((benzyloxy)carbonyl)oxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate | 1215016-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2,2,2-trichloroethyl ((2R,4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-(((benzyloxy)carbonyl)oxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate
• CAS: 1215016-51-5
• 化学式: C₂₇H₂₈Cl₃NO₉
• 分子量: 616.88
• InChiKey: BQBBWZFVDFJOJD-QALHXSLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl ((2R,4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-(((benzyloxy)carbonyl)oxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到C₂₇H₃₀Cl₃NO₉
  参考文献：
  名称：

  Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments

  摘要：

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.124
• 作为产物：
  描述：

  氯甲酸苄酯 、 allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-trichloroethyl ((2R,4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-(((benzyloxy)carbonyl)oxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate
  参考文献：
  名称：

  Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments

  摘要：

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.124