O-trichloroacetimidoyl-[(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-α-D-glucuronate | 850004-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-trichloroacetimidoyl-[(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-α-D-glucuronate
• CAS: 850004-42-1
• 化学式: C₇₁H₇₂Cl₃NO₁₈
• 分子量: 1333.71
• InChiKey: PHKIAVJYODDNPS-CBDQEUGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  93.0
• 可旋转键数：
  28.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  213.51
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  quillaic acid allyl ester 、 O-trichloroacetimidoyl-[(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-α-D-glucuronate 在 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以59%的产率得到O-(28-allylquillaic)-[(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：

  2,3,4-tri-O-benzyl-D-xylopyranose 在 2,4,6-三叔丁基吡啶 、 二苯基亚砜 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 4.72h， 生成 O-trichloroacetimidoyl-[(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-α-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 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.