allyl 3,4-O-isopropylidene-α-D-fucopyranoside | 201858-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl 3,4-O-isopropylidene-α-D-fucopyranoside
• 英文别名: allyl 6-deoxygalactoside；(3aS,4R,6S,7R,7aR)-2,2,4-trimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 201858-30-2
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: KNFMCAXCIHENKP-NZFPMDFQSA-N

物化性质

• 沸点：
  355.8±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 3,4-O-isopropylidene-α-D-fucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.49h， 生成 2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j
• 作为产物：
  描述：

  D-Fucose 在 对甲苯磺酸 、 乙酰氯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.5h， 生成 allyl 3,4-O-isopropylidene-α-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j

文献信息

• Synthesis and Antigenic Analysis of the BclA Glycoprotein Oligosaccharide from theBacillus anthracis Exosporium
  作者：Alok S. Mehta、Elke Saile、Wei Zhong、Therese Buskas、Russell Carlson、Elmar Kannenberg、Yvonne Reed、Conrad P. Quinn、Geert-Jan Boons

  DOI：10.1002/chem.200601245

  日期：2006.12.13

  not been found in spores of B. cereus and B. thuringiensis, making it a potential species-specific marker for B. anthracis. In order to study the antigenicity of anthrose, efficient syntheses of an anthrose-containing trisaccharide and a series of structurally related analogues were developed. The analogues lacked either the methyl ether at C-2 or contained modified C-4 amino functionalities of anthrose

  糖蛋白BclA是炭疽芽孢杆菌孢子孢子囊的重要组成部分。该糖蛋白被由β-L-鼠李糖苷组成的寡糖取代，该β-L-鼠李糖苷被先前未知的末端糖，2-O-甲基-4-（3-羟基-3-甲基丁酰胺基）-4,6-二脱氧-D-吡喃葡萄糖取代，也称为anthrose。在蜡状芽孢杆菌和苏云金芽孢杆菌的孢子中尚未发现炭疽病，使其成为炭疽芽孢杆菌潜在的物种特异性标记。为了研究蔗糖的抗原性，开发了含蔗糖的三糖和一系列结构上类似的类似物的有效合成方法。这些类似物在C-2处缺少甲基醚，或在炭疽中含有修饰的C-4氨基官能团。合成的化合物配备有氨丙基间隔基，以促进与海水养殖Keyhole帽贝血蓝蛋白（mcKLH）和牛血清白蛋白（BSA）的载体蛋白结合。用炭疽芽孢杆菌Sterne 34F（2）的活或辐射孢子免疫的兔的血清抗体能够识别合成的三糖-mcKLH缀合物。通过与游离的和与BSA结合的三糖的竞争性抑制，证实了相互作用的特异性
• Anthrax carbohydrates, synthesis and uses thereof
  申请人：UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：US09310366B2

  公开（公告）日：2016-04-12

  The present invention presents the isolation, characterization and synthesis of oligosaccharides of Bacillus anthracis. Also presented are antibodies that bind to such saccharide moieties and various methods of use for such saccharide moieties and antibodies.

  本发明提供了炭疽芽孢杆菌寡糖的分离、表征和合成。还提供了结合到这种糖基团的抗体，以及针对这种糖基团和抗体的各种使用方法。
• Synthesis of the Trisaccharide and Tetrasaccharide Moieties of the Potent Immunoadjuvant QS-21
  作者：Xiangming Zhu、Biao Yu、Yongzheng Hui、Richard R. Schmidt

  DOI：10.1002/ejoc.200300580

  日期：2004.3

  The title trisaccharide and tetrasaccharide moieties have been synthesized as part of our research programme to construct the complex triterpenoid saponin QS-21, a potent immunoadjuvant, which has been used in a series of clinical immunization trials. In view of the unwillingness of glucuronic acid as glycosyl acceptor, the branched glucuronic acid-containing trisaccharide 20 was synthesized from D-glucose

  标题三糖和四糖部分已合成作为我们研究计划的一部分，以构建复杂的三萜皂苷 QS-21，一种有效的免疫佐剂，已用于一系列临床免疫试验。鉴于葡萄糖醛酸不愿意作为糖基受体，由 D-葡萄糖合成含支链葡萄糖醛酸的三糖 20，其依次在 2 和 3 位糖基化，然后在 6 位氧化，线性序列为15 步，整体产量良好。含 apiose 的四糖 36 是通过线性糖基化策略从非还原性末端糖 D-apiose 构建的，D-apiose 是通过已知的程序从 D-木糖制备的，也是 15 个步骤的线性序列。(C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
• [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。
• Structurally Simple Benzyl-Type Photolabile Protecting Groups for Direct Release of Alcohols and Carboxylic Acids
  作者：Pengfei Wang、Wenya Lu、Dattatray A. Devalankar、Zhenying Ding

  DOI：10.1021/acs.orglett.5b00699

  日期：2015.5.1

  Structurally simple benzyl-type photolabile protecting groups (PPGs) have been developed to release alcohols and carboxylic acids. Release of two substrates from one PPG chromophore has also been accomplished.