(2S,3S)-2-[(1Z,3S)-3-(acetyloxy)hept-1-en-1-yl]-3,6-dihydro-6-oxo-2H-pyran-3-yl acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-[(1Z,3S)-3-(acetyloxy)hept-1-en-1-yl]-3,6-dihydro-6-oxo-2H-pyran-3-yl acetate
• 英文别名: (S,Z)-1-((2S,3S)-3-acetoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate；(S,Z)-1-[(2S,3S)-3-acetoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-1-en-3-yl acetate；6S-[(3S-acetyloxy)-1Z-heptenyl]-5S-(acetyloxy)-5,6-dihydro-2H-pyran-2-one；pectinolide A；[(2S,3S)-2-[(Z,3S)-3-acetyloxyhept-1-enyl]-6-oxo-2,3-dihydropyran-3-yl] acetate
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: ALTFKBHIGVQJSX-RTJHIJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[(1Z,3S)-3-(acetyloxy)hept-1-en-1-yl]-3,6-dihydro-6-oxo-2H-pyran-3-yl acetate 在 4-二甲氨基吡啶 、 双氧水 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 氘代吡啶 、 氘代氯仿 、 二氯甲烷 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2H-pyran-2-ones fromHyptisSpecies and Their Molecular Docking to α-Tubulin

  摘要：

  Cytotoxic 6-heptyl-5,6-dihydro-2H-pyran-2-ones are chemical markers of Hyptis (Lamiaceae) and are responsible for some of the therapeutic properties of species with relevance to traditional medicine. The present investigation describes the isolation of known pectinolides A-C (1-3), in addition to the new pectinolides I-M (4-8), from two Mexican collections of H. pectinata by HPLC. The novel biosynthetically related monticolides A (9) and B (10) were also isolated by high-speed countercurrent chromatography from H. monticola, an endemic species of the Brazilian southeastern high-altitude regions. A combination of chemical correlations, chiroptical measurements, and Mosher ester NMR analysis was used to confirm their absolute configuration. The utility of DFT-NMR chemical shifts and J(H-H) calculations was assessed for epimer differentiation. Molecular docking studies indicated that 6-hepty1-5,6-dihydro-2H-pyran-2-ones have a high affinity for the pironetin-binding site of alpha-tubulin, which may be a possible mechanism contributing to the cytotoxic potential of these small and flexible molecules.

  DOI：

  10.1021/acs.jnatprod.8b00908
• 作为产物：
  描述：

  (S)-(-)-1-heptyn-3-ol 在 2,6-二甲基吡啶 、 喹啉 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 乙基溴化镁 、 水 、 氢气 、 四氯化钛 、 sodium hydride 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 35.5h， 生成 (2S,3S)-2-[(1Z,3S)-3-(acetyloxy)hept-1-en-1-yl]-3,6-dihydro-6-oxo-2H-pyran-3-yl acetate
  参考文献：
  名称：

  First stereoselective total synthesis of pectinolide C and total synthesis of pectinolide A

  摘要：

  The first stereoselective synthesis of pectinolide C and synthesis of pectinolide A, from easily accessible 1-hexyne and D-mannitol are reported in a convergent manner. The salient features include acetylenic addition to the chiral aldehyde and Still-Gennari olefination. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.039

文献信息

• Stereoselective Total Synthesis of Pectinolides A, C, and H
  作者：Ramesh Saudagar Ghogare、Sachin Bibishan Wadavrao、Akkirala Venkat Narsaiah

  DOI：10.1002/hlca.201500110

  日期：2016.4

  A simple and straightforward stereoselective total synthesis of Pectinolides A, C, and H is described. The synthesis has been started from commercially available (+)‐diethyl l‐tartrate and involves Ohira–Bestmann reaction, Corey–Bakshi–Shibata (CBS) reduction, and Still–Gennari olefination as key steps.

  描述了简单，直接的果胶内酯A，C和H的立体选择性全合成。合成是从市售的酒石酸（+）-二乙基l-酒石酸开始的，其中涉及Ohira – Bestmann反应，Corey – Bakshi – Shibata（CBS）还原以及Still – Gennari烯化反应为关键步骤。
• The First Total Synthesis of Pectinolides D and E and Total Synthesis of Pectinolides A and C
  作者：Gowravaram Sabitha、Praveen AnkiReddy、Sukant Das

  DOI：10.1055/s-0034-1378912

  日期：——

  The first total synthesis of pectinolides D and E and total synthesis of pectinolides A and C was achieved from a hitherto unknown common key building block prepared from readily available d-mannitol. Key reactions involved in the synthesis are Red-Al reduction of an epoxy alcohol, enantioselective Noyori reduction of ynones, aldehyde–alkyne coupling, and Still–Genari cis-olefination. The first total

  摘要 通过迄今未知的由容易获得的d-甘露糖醇制备的共同关键结构单元，实现了果皮内酯D和E的首次全合成和果皮内酯A和C的全合成。合成过程中的关键反应是环氧醇的Red-Al还原，炔酮的对映选择性Noyori还原，醛-炔烃偶联和Still-Genari顺式烯烃化。 通过迄今未知的由容易获得的d-甘露糖醇制备的共同关键结构单元，实现了果皮内酯D和E的首次全合成和果皮内酯A和C的全合成。合成过程中的关键反应是环氧醇的Red-Al还原，炔酮的对映选择性Noyori还原，醛-炔烃偶联和Still-Genari顺式烯烃化。
• Anti-Staphylococcal and Cytotoxic Compounds from<i>Hyptis pectinata</i>
  作者：Mabel Fragoso-Serrano、Simon Gibbons、Rogelio Pereda-Miranda

  DOI：10.1055/s-2005-837831

  日期：2005.3

  32-64 microg/mL. The absolute stereochemistry of this new compound was established as 5 S-[(4 S-acetyloxy)-(1 S-hydroxy)-2 Z-octenyl]-2(5 H)-furanone on the basis of spectral, chiroptical data and chemical correlation with pectinolide A ( 1). Mosher ester derivatives were used with pectinolide B ( 2) for confirmation of the 3'-( S) absolute stereochemistry on the side chain chiral center of pectinolides

  从墨西哥药用植物Hyptis pectinata制备的CHCl（3）提取物的生物测定指导分馏导致分离出四个吡喃酮，果胶内酯AC（1-3）和H（4）。使用培养的KB细胞追踪活性。在32-64 microg / mL的浓度范围内，对金黄色葡萄球菌具有多重耐药性的菌株对果胶内酯H（4; KB> 20 microg / mL）敏感。该新化合物的绝对立体化学是根据光谱，手性数据和光谱数据确定为5 S-[（4 S-乙酰氧基）-（1 S-羟基）-2 Z-辛烯基] -2（5 H）-呋喃酮。与果胶内酯A的化学相关性（1）。Mosher酯衍生物与果胶内酯B（2）一起用于确认果胶内酯AC的侧链手性中心的3'-（S）绝对立体化学。
• First stereoselective total synthesis of pectinolide A
  作者：J.S. Yadav、S.S. Mandal

  DOI：10.1016/j.tetlet.2011.08.036

  日期：2011.11

  The enantioselective synthesis of bio-active 5,6-dihydro-alpha-pyrone, pectinolide A, has been achieved in 10 steps in good overall yield. Of the three stereogenic centres, the C-5/C-6 vic-diol was obtained using dia-stereo- and enantioselective Brown hydroxyl crotylation, while the C-3' stereocentre was created by Jacobsen hydrolytic kinetic resolution method. (C) 2011 Elsevier Ltd. All rights reserved.
• The stereoselective total syntheses of pectinolides A, B, and C
  作者：Udugu Ramulu、Dasari Ramesh、Sudina Purushotham Reddy、Singanaboina Rajaram、Katragadda Suresh Babu

  DOI：10.1016/j.tetasy.2014.09.009

  日期：2014.10

  The stereoselective total synthesis of pectinolide B has been accomplished for the first time along with total syntheses of pectinolides A and C. MacMillan alpha-hydroxylation and Sharpless asymmetric dihydroxylation reactions are involved in generating the three stereogenic centers. Other important transformations in the synthesis are Z-selective Still-Gennari olefination, selective benzylation of the homoallylic alcohol, and a one-pot MOM deprotection followed by lactonization leading to all three pectinolides A-C being synthesized from a common intermediate. Pectinolides A, B, and C were synthesized from n-hexanal in 19, 20, and 18 steps with overall yields of 8.8%, 6.72%, and 9.2%, respectively. (C) 2014 Elsevier Ltd. All rights reserved.