(4S,3R)-4-benzyloxypent-1-en-3-ol | 403694-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,3R)-4-benzyloxypent-1-en-3-ol
• 英文别名: (3R,4S)-4-(benzyloxy)-1-penten-3-ol；(4S)-4-(benzyloxy)pent-1-en-3-ol；(3R,4S)-4-(benzyloxy)pent-1-en-3-ol；(3R,4S)-4-phenylmethoxypent-1-en-3-ol
• CAS: 403694-73-5
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: HLNDXQGUABEOGX-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,3R)-4-benzyloxypent-1-en-3-ol 在 咪唑 、 4-二甲氨基吡啶 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.0h， 生成 (1S,2R)-2-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-methyl-3-butenyl (E,5S)-5-[(3R)-3-(acryloyloxy)butanoyl]oxy-2-hexenoate
  参考文献：
  名称：

  RCM mediated synthesis of macrosphelides I and G

  摘要：

  The total synthesis of 16-membered macrolides, macraosphelides I and G, has been achieved starting from ethyl-(S)-lactate and (S)- malic acid. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centres, while Yamaguchi esterification and ring-closing metathesis strategies were used for the construction of the lactone ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.017
• 作为产物：
  描述：

  (2E,4S)-4-<(benzyl)oxy>-2-pentenol 在 titanium(IV) isopropylate 、 四氯化碳 、 过氧化氢异丙苯 、 sodium 、 碳酸氢钠 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (4S,3R)-4-benzyloxypent-1-en-3-ol
  参考文献：
  名称：

  RCM mediated synthesis of macrosphelides I and G

  摘要：

  The total synthesis of 16-membered macrolides, macraosphelides I and G, has been achieved starting from ethyl-(S)-lactate and (S)- malic acid. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centres, while Yamaguchi esterification and ring-closing metathesis strategies were used for the construction of the lactone ring. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.017

文献信息

• De novo synthesis of novel bacterial monosaccharide fusaminic acid
  作者：Ruohan Wei、Han Liu、Xuechen Li

  DOI：10.1038/s41429-019-0170-3

  日期：2019.6

  an oral bacteria related to various types of diseases. As Gram-negative bacteria, lipopolysaccharide (LPS) of Fusobacterium nucleatum could be a potential virulence factor. Recently, the structure of O-antigen in LPS of Fusobacterium nucleatum strain 25586 was elucidated to contain a trisaccharide repeating unit -(4-β-Nonp5Am-4-α-L-6dAltpNAc3PCho-3-β-D-QuipNAc)-. The nonulosonic acid characterized as

  核梭菌是一种与各种疾病有关的口腔细菌。作为革兰氏阴性菌，核梭菌的脂多糖（LPS）可能是潜在的致病因子。最近，阐明了核梭状芽胞杆菌菌株25586的LPS中的O-抗原结构，其包含三糖重复单元-（4-β-Nonp5Am-4-α-L-6dAltpNAc3PCho-3-β-D-QuipNAc）-。表征为5-乙酰氨基-3,5,9-三苯氧基-L-甘油-L-葡萄糖-非-2-磺酸的壬二酸（命名为fusaminic acid）和2-乙酰氨基-2,6-dideoxy-L -altrose是分离的新型单糖。在本文中，我们报道了5-N-乙酰基次品酸和硫代糖苷衍生物的从头合成，以进一步研究壬二酸对细菌发病的生物学意义。
• Asymmetric Total Synthesis of (+)-Brefeldin A from (<i>S</i>)-Lactate by Triple Chirality Transfer Process and Nitrile Oxide Cycloaddition^,¹
  作者：Deukjoon Kim、Jongkook Lee、Phil Jong Shim、Joong Inn Lim、Hyunil Jo、Sanghee Kim

  DOI：10.1021/jo010743i

  日期：2002.2.1

  A novel synthesis of (+)-brefeldin A (1) has been accomplished on the basis of triple chirality transfer methodology, intramolecular ester enolate alkylation, and both intra- and intermolecular nitrile oxide cycloaddition strategies.

  （+）-布雷菲德菌素A（1）的新型合成已基于三重手性转移方法，分子内酯烯酸酯烷基化以及分子内和分子间一氧化氮环加成策略完成。
• Picolinamide compounds with fungicidal activity
  申请人：DOW AGROSCIENCES LLC

  公开号：US10433555B2

  公开（公告）日：2019-10-08

  This disclosure relates to picolinamides of Formula I and their use as fungicides.

  本公开涉及式 I 的吡啶酰胺及其作为杀菌剂的用途。
• Asymmetric total syntheses of aspilactonol F and aspiketolactonol and synthetic studies toward diplofuranoxin
  作者：Sagar B. Khandekar、Rodney A. Fernandes

  DOI：10.1039/d4ob00549j

  日期：——

  The first asymmetric total synthesis of C9 polyketides, aspilactonol F and aspiketolactonol has been achieved. Ring-closing-metathesis has been employed as the key step in the synthesis. The total synthesis of aspilactonol F and aspiketolactonol was accomplished in 8 and 10 steps, in good overall yields of 28% and 24%, respectively, with only four column purifications for the former. A common strategy

  首次实现了C 9聚酮化合物、阿司匹内酯F和阿司匹内酯的不对称全合成。闭环复分解已被用作合成中的关键步骤。阿司匹内酯 F 和阿司匹酮内酯的全合成通过 8 步和 10 步完成，总收率分别为 28% 和 24%，前者仅经过四次柱纯化。还提出了双氟呋喃辛关键中间体的简洁合成的通用策略。