allyl D-fucopyranoside | 207505-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl D-fucopyranoside
• 英文别名: (2R,3R,4S,5R)-2-methyl-6-prop-2-enoxyoxane-3,4,5-triol
• CAS: 207505-60-0
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: JPOJNSPEUPRVLQ-MBOVONDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl D-fucopyranoside 在 四(三苯基膦)钯 咪唑 、 4-二甲氨基吡啶 、 3 A molecular sieve 、 四丁基氟化铵 、 diethylzinc 、 二正丁基氧化锡 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 163.75h， 生成 4-O-acetyl-3-O-benzyl-α-D-fucopyranose
  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：

  D-Fucose 、 烯丙醇 在 乙酰氯 作用下， 生成 allyl D-fucopyranoside
  参考文献：
  名称：

  [EN] TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS
  [FR] SYNTHÈSE DE SAPONINE TRITERPÉNIQUE, INTERMÉDIAIRES ET COMBINAISONS D'ADJUVANTS

  摘要：

  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。

  公开号：

  WO2018191598A1

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。
• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• [EN] SAPONIN-BASED VACCINE ADJUVANTS<br/>[FR] ADJUVANTS DE VACCIN À BASE DE SAPONINES
  申请人：UAB RES FOUND

  公开号：WO2019183159A1

  公开（公告）日：2019-09-26

  Provided are variants of saponins that are found in Quillaja saponaria (QS) Molina tree bark that are chemically modified to distinguish them from naturally occurring parent saponins. The modified saponins have increased adjunctive activity compared to the unmodified parent saponins. Defined structures allow for comparisons of the modifying groups with respect to their respective adjunct activity and permit characterized vaccine formulations that have one or more defined saponins.

  提供了在Quillaja saponaria (QS) Molina树皮中发现的皂苷的变种，这些皂苷经过化学修饰，以使它们与自然存在的原始皂苷有所区别。经过修改的皂苷与未经修改的原始皂苷相比具有增强的辅助活性。定义的结构允许对修饰基团进行比较，以确定它们各自的辅助活性，并允许确定具有一个或多个定义的皂苷的疫苗配方。
• TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF
  申请人：Gin David

  公开号：US20110300177A1

  公开（公告）日：2011-12-08

  The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

  本发明涉及三萜糖苷皂苷衍生的佐剂、其合成、中间体及其用途。QS-7是一种强效的免疫佐剂，其毒性显著低于QS-21，QS-21是目前在抗癌和抗病毒疫苗中被广泛使用的相关皂苷佐剂。繁琐的分离和纯化方案阻碍了QS-7的临床开发。本发明提供了一种新的半合成方法，其中使用水解的原皂苷混合物来合成QS-7、QS-21和相关的类似物，极大地促进了QS-7和QS-21类似物的临床前和临床评估。
• TRITERPENE SAPONINS, METHODS OF SYNTHESIS AND USES THEREOF
  申请人：MEMORIAL SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH

  公开号：US20150086585A1

  公开（公告）日：2015-03-26

  The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

  本发明涉及以三萜甙苷皂苷为基础的佐剂，其合成，中间体以及使用方法。 QS-7是一种强效的免疫佐剂，其毒性明显低于QS-21，QS-21是当前抗癌和抗病毒疫苗中受欢迎的佐剂。繁琐的分离和纯化协议阻碍了QS-7的临床开发。提供了一种新的半合成方法，其中使用水解的原皂苷混合物来合成QS-7，QS-21和相关类似物，极大地促进了QS-7和QS-21类似物的临床前和临床评估。