acetic acid 4-benzyloxy-5-hydroxy-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester | 912805-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid 4-benzyloxy-5-hydroxy-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester
• CAS: 912805-51-7
• 化学式: C₂₂H₂₅NO₈
• 分子量: 431.442
• InChiKey: ADWXJOQNAIDZSV-UACIBIBWSA-N

物化性质

• 沸点：
  561.8±50.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  acetic acid 4-benzyloxy-5-hydroxy-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester 、 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.25h， 以153 mg的产率得到
  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：

  (2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol 在 咪唑 、 4-二甲氨基吡啶 、 四丁基溴化铵 、 二正丁基氧化锡 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 79.25h， 生成 acetic acid 4-benzyloxy-5-hydroxy-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester
  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