triisopropylsilyl 2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-β-L-rhamnopyranoside | 850004-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: triisopropylsilyl 2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-β-L-rhamnopyranoside
• 英文别名: O-triisopropylsilyl [2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)]-O-[2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)]-O-2,3-O-isopropylidene-β-L-rhamnopyranoside；[(2S,3R,4R)-2-[(2S,3R,4S,5R)-2-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-tri(propan-2-yl)silyloxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-4-acetyloxy-4-(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 850004-34-1
• 化学式: C₅₃H₇₄O₁₅Si
• 分子量: 979.247
• InChiKey: RHGBWTBRTVYIQK-QVASDHPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  69
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  triisopropylsilyl 2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-β-L-rhamnopyranoside 在 2,4,6-三叔丁基吡啶 、 二苯基亚砜 、 四丁基氟化铵 、 水 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.05h， 生成
  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：

  4-O-acetyl-2,3-O-isopropylidene-L-rhamnopyranose 在 咪唑 、 水 、 三乙基硅基三氟甲磺酸酯 、 potassium carbonate 、 silver nitrate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 triisopropylsilyl 2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-β-L-rhamnopyranoside
  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 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.