O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate | 351900-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate
• 英文别名: methyl (2S,3R,4R,5R,6R)-3-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-[(4-methoxyphenyl)methoxy]oxane-2-carboxylate
• CAS: 351900-92-0
• 化学式: C₂₃H₃₆O₉Si
• 分子量: 484.619
• InChiKey: INDWGBBQIQSBTJ-JXDTVZCFSA-N

物化性质

• 沸点：
  524.4±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 在 水 、 氟化氢吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 4.72h， 生成 O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1-3)]-6-O-methyl-4-O-acetyl-D-glucuronate
  参考文献：
  名称：

  Synthetic Studies of Complex Immunostimulants from Quillaja saponaria:  Synthesis of the Potent Clinical Immunoadjuvant QS-21A_api

  摘要：

  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.

  DOI：

  10.1021/ja062364i
• 作为产物：
  描述：

  methyl 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal 在 2,4,6-三叔丁基吡啶 、 二苯基亚砜 、 trifluoromethanesulfonic acid anhydride 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 11.2h， 生成 O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate
  参考文献：
  名称：

  Synthetic Studies of Complex Immunostimulants from Quillaja saponaria:  Synthesis of the Potent Clinical Immunoadjuvant QS-21A_api

  摘要：

  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.

  DOI：

  10.1021/ja062364i

文献信息

• Synthesis of the Trisaccharide Portion of the Immunologic Adjuvant QS-21A via Sulfonium-Mediated Oxidative and Dehydrative Glycosylation
  作者：Yong-Jae Kim、David Y. Gin

  DOI：10.1021/ol015651u

  日期：2001.6.1

  [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.