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

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1Z,3S)-1-[(2S,3S)-3,6-dihydro-3-hydroxy-6-oxo-2H-pyran-2-yl]hept-1-en-3-yl acetate
• 英文别名: (S,Z)-1-((2S,3S)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate；(S,Z)-1-[(2S,3S)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-1-en-3-yl acetate；pectinolide C；[(Z,3S)-1-[(2S,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl] acetate
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: DYWKRIWLCNEWRY-SHYGTOARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1Z,3S)-1-[(2S,3S)-3,6-dihydro-3-hydroxy-6-oxo-2H-pyran-2-yl]hept-1-en-3-yl acetate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以90%的产率得到(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：

  果胶内酯A，C和H的立体选择性全合成

  摘要：

  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。

  DOI：

  10.1002/hlca.201500110
• 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 34.5h， 生成 (1Z,3S)-1-[(2S,3S)-3,6-dihydro-3-hydroxy-6-oxo-2H-pyran-2-yl]hept-1-en-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

• 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。
• Stereoselective synthesis of pectinolide C
  作者：T. Vijaya Kumar、G. Shankaraiah、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2012.12.114

  日期：2013.3

  The first total synthesis of the pectinolide C has been accomplished using the silyl-tethered ring closing metathesis, Jacobsen resolution, and Wadsworth-Emmons olefinations as key reaction sequences. (C) 2013 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.
• First stereoselective total synthesis of pectinolide C and total synthesis of pectinolide A
  作者：Gowravaram Sabitha、Sukant Kishore Das、Praveen AnkiReddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2012.12.039

  日期：2013.2

  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.
• 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。