Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester | 544686-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxypropan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 544686-92-2
• 化学式: C₆₁H₇₇N₂O₉PSi
• 分子量: 1041.35
• InChiKey: IOLXBCIDZWPTHC-AKGZIXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.14
• 重原子数：
  74
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester 、 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA)

  摘要：

  Based on 1,2-O-isopropylidene-sn-glyerol, which is readily available from D-mannitol, five chiral building blocks for the construction of structural variants of Staphylococcus aureus LTA designed and synthesized. Ligation of these building blocks led readily to the target molecules 1 and 2. They demonstrated that the D-alanine residues at the glycerophosphate backbone are decisive for the activation of the immune system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.070
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 1,3-丙二硫醇 、 Wilkinson's catalyst 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium methylate 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester
  参考文献：
  名称：

  合成第一个完全活性的脂磷壁酸。

  摘要：

  DOI：

  10.1002/anie.200390243

文献信息

• A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues
  作者：A STADELMAIER、I FIGUEROAPEREZ、S DEININGER、S VONAULOCK、T HARTUNG、R SCHMIDT

  DOI：10.1016/j.bmc.2006.05.055

  日期：2006.9.15

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.