triisopropylsilanyl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside | 850004-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: triisopropylsilanyl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside
• 英文别名: triisopropyl 4-O-acetyl-3-O-benzyl-β-D-fucopyranose；(2R,3S,4R,5R,6S)-4-(benzyloxy)-5-hydroxy-2-methyl-6-[(triisopropylsilyl)oxy]oxan-3-yl acetate；[(2R,3S,4R,5R,6S)-5-hydroxy-2-methyl-4-phenylmethoxy-6-tri(propan-2-yl)silyloxyoxan-3-yl] acetate
• CAS: 850004-32-9
• 化学式: C₂₄H₄₀O₆Si
• 分子量: 452.663
• InChiKey: RUMNWRMVKXZSAJ-MWFZDGHISA-N

物化性质

• 沸点：
  494.1±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  triisopropylsilanyl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside 在 2,4,6-三叔丁基吡啶 、 三氟甲磺酸酐 、 二苯基亚砜 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of the Potent Immunostimulatory Adjuvant QS-21A

  摘要：

  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.

  DOI：

  10.1021/ja0422007
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol 在 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 tert-butyl-ammonium fluoride 、 四丁基溴化铵 、 二正丁基氧化锡 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.25h， 生成 triisopropylsilanyl 4-O-acetyl-3-O-benzyl-β-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of the Potent Immunostimulatory Adjuvant QS-21A

  摘要：

  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.

  DOI：

  10.1021/ja0422007

文献信息

• [EN] TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS<br/>[FR] SYNTHÈSE DE SAPONINE TRITERPÉNIQUE, INTERMÉDIAIRES ET COMBINAISONS D'ADJUVANTS
  申请人：ADJUVANCE TECH INC

  公开号：WO2018191598A1

  公开（公告）日：2018-10-18

  The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

  本申请涉及三萜甙苷皂苷衍生的佐剂、其合成以及中间体。该申请还提供了包含本发明化合物的药物组合物，以及使用这些化合物或组合物在治疗和免疫传染病方面的方法。
• 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 QS-21-Xylose: Establishment of the Immunopotentiating Activity of Synthetic QS-21 Adjuvant with a Melanoma Vaccine
  作者：Kai Deng、Michelle M. Adams、Payal Damani、Philip O. Livingston、Govind Ragupathi、David Y. Gin

  DOI：10.1002/anie.200801885

  日期：2008.8.11