2,3-O-isopropylidene-D-apiofuranose | 70147-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-D-apiofuranose
• 英文别名: (3aR,6aR)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-6-ol
• CAS: 70147-50-1
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: QCNHIMWAKKHAFC-OHEWIBQUSA-N

物化性质

• 沸点：
  327.1±42.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-D-apiofuranose 在 吡啶 、 copper(l) iodide 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸酐 为溶剂， 反应 132.5h， 生成 (3R,4R)-2-Methoxy-4-methylsulfanylmethoxy-4-nonyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Pak-Tsun Ho; Wong, Canadian Journal of Chemistry, 1985, vol. 63, # 8, p. 2221 - 2224

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-1-((S)-5,5-Bis-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol 在 sodium periodate 作用下， 以 水 为溶剂， 生成 2,3-O-isopropylidene-D-apiofuranose
  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

• Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
  作者：Peter Kis、Elena Potocká、Vladimír Mastihuba、Mária Mastihubová

  DOI：10.1016/j.carres.2016.04.030

  日期：2016.7

  4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step-benzoylation of primary hydroxyl of 2,3-isopropylidene-α,β-d-apiofuranose catalysed by Lipolase 100T and stereoselective β-d-apiofuranosylation

  通过五个反应序列，由2,3-异亚丙基-α，β-d-呋喃呋喃糖以61％的收率制备了4-硝基苯基β-d-呋喃呋喃糖苷作为检测β-d-呋喃糖苷酶活性的生色探针。合成涉及一种由Lipolase 100T催化的2,3-异亚丙基-α，β-d-呋喃呋喃糖伯羟基的区域选择性酶促步骤苯甲酰化和使用BF3·OEt2 / Et3N的对硝基苯酚的立体选择性β-d-呋喃呋喃糖基化。该产物用于筛查61种粗制商业酶和植物材料样品中的β-d-apiofuranosidase活性。源自曲霉属不同菌株的十五种酶制剂显示出β-d-呋喃呋喃糖苷酶活性。在Rapidase AR 2000（78.27 U / g）和冻干的Viscozyme L（64,36 U / g）中发现了最高的活性。
• 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] TUBERCULATIN ANALOGS AS ANTIVIRAL AGENTS<br/>[FR] ANALOGUES DE LA TUBERCULINE UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV HONG KONG BAPTIST UNIV

  公开号：WO2022135136A1

  公开（公告）日：2022-06-30

  Provided herein are tuberculatin analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.

  本文提供了一些类结核菌素的模拟物，可用作抗病毒剂，例如抗HIV、抗冠状病毒、抗埃博拉病毒和抗流感病毒的药物，并提供了使用方法。
• Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
  作者：K. Victoria Booth、Sarah F. Jenkinson、Daniel Best、Fernando Fernández Nieto、Ramón J. Estévez、Mark R. Wormald、Alexander C. Weymouth-Wilson、George W.J. Fleet

  DOI：10.1016/j.tetlet.2009.06.098

  日期：2009.9

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthetic Studies of Complex Immunostimulants from <i>Quillaja saponaria</i>:  Synthesis of the Potent Clinical Immunoadjuvant QS-21A_a_pi
  作者：Yong-Jae Kim、Pengfei Wang、Mauricio Navarro-Villalobos、Bridget D. Rohde、DerryBerry、David Y. Gin

  DOI：10.1021/ja062364i

  日期：2006.9.1

  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.