thexyldimethylsilyl 2-azido-3-O-[(1R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 478920-16-0

• 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: thexyldimethylsilyl 2-azido-3-O-[(1R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: (2R)-2-[[(4aR,6S,7R,8R,8aS)-7-azido-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoic acid
• CAS: 478920-16-0
• 化学式: C₂₀H₃₇N₃O₇Si
• 分子量: 459.615
• InChiKey: TUPIFDURQFTRAH-KKHNULJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl 2-azido-3-O-[(1R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 吡啶 、 lithium hydroxide 、 硫化氢 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 54.0h， 生成 thexyldimethylsilyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-[(2R)-propionyl-(L-alanine)-2-yl]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

  摘要：

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8
• 作为产物：
  描述：

  thexyldimethylsilyl 2-azido-2-deoxy-4,6-O-isopropilidene-3-O-[(1R)-1-(methoxycarbonyl)ethyl]β-D-glucopyranoside 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 以100%的产率得到thexyldimethylsilyl 2-azido-3-O-[(1R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

  摘要：

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

文献信息

• Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid
  作者：Niels Kubasch、Richard R. Schmidt

  DOI：10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

  日期：2002.8

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.