(2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol | 132938-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol
• CAS: 132938-42-2
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: UAUNFBKCVKLPBF-BIRIHMBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  122.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.75h， 生成 (2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol
  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：

  2-nitrobenzyl 2,3,4-tri-O-acetyl-β-D-fucopyranose 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol
  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

• Kaneko, Toshio; Takahashi, Kazunobu; Hirama, Masahiro, Heterocycles, 1998, vol. 47, # 1, p. 91 - 96
  作者：Kaneko, Toshio、Takahashi, Kazunobu、Hirama, Masahiro

  DOI：——

  日期：——
• 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.
• Nicolaou, K. C.; Schreiner, E. P.; Stahl, W., Angewandte Chemie, 1991, vol. 103, # 5, p. 566 - 568
  作者：Nicolaou, K. C.、Schreiner, E. P.、Stahl, W.

  DOI：——

  日期：——