O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate | 351900-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-3-acetyloxy-5-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-hydroxy-6-[(4-methoxyphenyl)methoxy]oxane-2-carboxylate
• CAS: 351900-97-5
• 化学式: C₅₁H₅₄O₁₅
• 分子量: 906.981
• InChiKey: DXZFLTFCXQPPBQ-RTQVMUSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 在 2,4,6-三叔丁基吡啶 、 三氟甲磺酸酐 、 二苯基亚砜 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 4.63h， 生成 O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzoyl-β-D-xylosyl)-(1->3)]-6-O-methyl-4-O-acetyl-α-D-glucuronate
  参考文献：
  名称：

  Synthesis of the Trisaccharide Portion of the Immunologic Adjuvant QS-21A via Sulfonium-Mediated Oxidative and Dehydrative Glycosylation

  摘要：

  [GRAPHICS]The first synthesis of the trisaccharide fragment of the potent immunologic adjuvant QS-PIA is reported. The key steps involve the application of sulfonium-mediated oxidative and dehydrative glycosidic couplings to construct the anomeric linkages in a short and convergent assembly of the branched trisaccharide.

  DOI：

  10.1021/ol015651u
• 作为产物：
  描述：

  O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 在 2,4,6-三叔丁基吡啶 、 三氟甲磺酸酐 、 二苯基亚砜 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 、 氯仿 为溶剂， 反应 5.5h， 生成 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate
  参考文献：
  名称：

  Synthesis of the Trisaccharide Portion of the Immunologic Adjuvant QS-21A via Sulfonium-Mediated Oxidative and Dehydrative Glycosylation

  摘要：

  [GRAPHICS]The first synthesis of the trisaccharide fragment of the potent immunologic adjuvant QS-PIA is reported. The key steps involve the application of sulfonium-mediated oxidative and dehydrative glycosidic couplings to construct the anomeric linkages in a short and convergent assembly of the branched trisaccharide.

  DOI：

  10.1021/ol015651u

文献信息

• Synthetic Studies of Complex Immunostimulants from <i>Quillaja saponaria</i>:  Synthesis of the Potent Clinical Immunoadjuvant QS-21A_a_pi
  作者：Yong-Jae Kim、Pengfei Wang、Mauricio Navarro-Villalobos、Bridget D. Rohde、DerryBerry、David Y. Gin

  DOI：10.1021/ja062364i

  日期：2006.9.1

  QS-21 is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing vaccine therapy clinical trials involving QS-21 as a critical adjuvant component for immune response augmentation. QS-21 is a natural product immunostimulatory adjuvant, eliciting both T-cell- and antibody-mediated immune responses with microgram doses. Herein is reported the synthesis of QS-21A(api) in a highly modular strategy, applying novel glycosylation methodologies to a convergent construction of the potent saponin immunostimulant. The chemical synthesis of QS-21 offers unique opportunities to probe its mode of biological action through the preparation of otherwise unattainable nonnatural saponin analogues.
• Synthesis of the Potent Immunostimulatory Adjuvant QS-21A
  作者：Pengfei Wang、Yong-Jae Kim、Mauricio Navarro-Villalobos、Bridget D. Rohde、David Y. Gin

  DOI：10.1021/ja0422007

  日期：2005.3.1

  QS-21A is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy, given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing clinical trials involving QS-21A as a critical component for immune response augmentation in microgram doses. Herein is reported the first synthesis and structure verification of QS-21Aapi, applying novel glycosylation methodologies in the convergent modular construction of this rare and potent natural product immunostimulant.