(4R,6S)-2,4-二甲氧基-6-甲基四氢-2H-吡喃 | 237056-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: (4R,6S)-2,4-二甲氧基-6-甲基四氢-2H-吡喃
• 英文名称: (2S,4R,6RS)-2-methyl-4,6-dimethoxytetrahydropyran
• 英文别名: (4R,6S)-2,4-(dimethoxy)-6-methyltetrahydropyran；2H-Pyran,tetrahydro-2,4-dimethoxy-6-methyl-,(4R,6S)-(9CI)；(4R,6S)-2,4-dimethoxy-6-methyloxane
• CAS: 237056-36-9
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: FBZVZMDKKTZELT-KJFJCRTCSA-N

物化性质

• 沸点：
  195.9±40.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,6S)-2,4-二甲氧基-6-甲基四氢-2H-吡喃 在 三氟甲磺酸三甲基硅酯 2,6-二甲基吡啶 、 二甲基硫 、 碳酸氢钠 、 臭氧 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 、 苯 为溶剂， 反应 54.2h， 生成 (E)-(2S,3S,4R,5R)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoct-6-ene
  参考文献：
  名称：

  A stereocontrolled synthesis of a C19-C32 / C17-C30 Segment for swinholide A and misakinolide A, Cytotoxic dimeric macrolides from theonella swinhoei.

  摘要：

  The C19-C32/C-17-C30 segment (-)-5 of swinholide A/misakinolide A was prepared in 15 steps (6% yield) from (+/-)-13. Key steps include the Sharpless epoxidation, 13 --> 14, the acetal allylation, 12 --> 16, the anti aldol, 17 + 11 --> 9, and the alkene hydroboration, 19 --> 20.

  DOI：

  10.1016/s0040-4039(00)78876-9
• 作为产物：
  描述：

  (3R,5S)-tert-butyl 3,5-dihydroxyhexanoate 在 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 69.67h， 生成 (4R,6S)-2,4-二甲氧基-6-甲基四氢-2H-吡喃
  参考文献：
  名称：

  使用 alyronine a-swinholide A 杂化物对抗肿瘤海洋大环内酯的构效关系研究

  摘要：

  设计、合成和生物学评估了由 alyronine A 的大环内酯部分和 swinholide A 的侧链部分组成的 alyronine A-swinholide A 杂化物。这种杂合体以与 alyronine A 相同的方式诱导两种主要细胞骨架蛋白肌动蛋白和微管蛋白之间的蛋白质相互作用，并表现出强大的细胞毒性和肌动蛋白解聚活性。N、N、O中甲氧基的重要性-三甲基丝氨酸酯通过使用杂合类似物的氨基酸部分的构效关系研究得到澄清。此外，比较 alyronine A 和 swinholide A 的侧链类似物的肌动蛋白解聚活性表明，swinholide A 的侧链类似物的肌动蛋白解聚活性比 alyronine A 弱得多。

  DOI：

  10.1039/d2ob00118g

文献信息

• The total synthesis of swinholide A. Part 1: A stereocontrolled synthesis of a C19-C32 segment
  作者：Ian Paterson、John G. Cumming、Richard A. Ward、Serge Lamboley

  DOI：10.1016/0040-4020(95)00546-k

  日期：1995.8

  The C19-C32 segment 10 of swinholide A was prepared in 15 steps (8% yield, 82% ds) from (±)-16. Key steps include (i) the Sharpless epoxidation, 16 → 17, (ii) the acetal allylation, 15 → 23, (iii) the anti aldol addition, 13 + 14 → 12, and (iv) the alkene hydroboration, 30 → 31. The swinholides are a series of complex polyketide macrodiolides, which display potent cytotoxicity against a variety of

  从（±）-16分15步（产率为8％，产率为82％ds）制备了Swinholide A的C 19 -C 32链段10。关键步骤包括（i）Sharpless环氧化16 → 17，（ii）乙缩醛烯丙基化15 → 23，（iii）抗羟醛加成13 + 14→12和（iv）烯烃硼氢化30→31。swinholides是一系列复杂的聚酮大环氧化物，对多种人类肿瘤细胞系均显示出强大的细胞毒性。1,2从海洋海绵中分离出的Swinholide A1985年，Carmely和Kashman首次报道了Theonella swinhoei作为抗真菌剂。1使用NMR方法和化学方法
• Development of a novel inducer of protein–protein interactions based on aplyronine A
  作者：Takayuki Ohyoshi、Atsuhiro Takano、Mayu Namiki、Tomotaka Ogura、Yuto Miyazaki、Yuta Ebihara、Koichi Takeno、Ichiro Hayakawa、Hideo Kigoshi

  DOI：10.1039/c8cc04613a

  日期：——

  An aplyronine A–swinholide A hybrid, consisting of the macrolactone part of aplyronine A and the side chain part of swinholide A, was designed, synthesized, and evaluated for biological activities.

  一个由aplyronine A的大环内酯部分和swinholide A的侧链部分组成的混合物被设计、合成并用于生物活性评估。
• Synthetic Studies toward the Total Synthesis of Swinholide. 1. Stereoselective Construction of the C₁₉−C₃₅ Subunit
  作者：Gary E. Keck、Gregory D. Lundquist

  DOI：10.1021/jo990291y

  日期：1999.6.1

  The development of an approach directed at the total synthesis of the complex cytotoxic marine macrodiolide swinholide is described. The present study focuses on the development of a synthetic route far the preparation of the C-19-C-35 segment of the structure, which is composed of a trisubstituted pyran moiety with a contrathermodynamic anti arrangement of the C-2 and C-6 pyran substituents (swinholide C-27 and C-31) which is joined by an ethano linker to an acyclic array containing five contiguous stereocenters. The pyran subunit was constructed using a stereoselective allylation of a beta-alkoxy aldehyde with 1,3-asymmetric induction and a second stereoselective allylation to prepare the C-glycosidic type of linkage. Use of the Hafner-Duthaler reagent was investigated as a potential means of constructing the anti vicinal hydroxyl-methyl relationships found in the C-19-C-24 Segment but was found not to be practical in this instance. The Evans bis propionate methodology was used to introduce a four-carbon unit, and a Mukaiyama aldol was used for chain extension to incorporate the remaining two carbons and two stereocenters of this segment. Attempted use of the Hanessian benzylidene acetal fragmentation reaction in this sequence was thwarted by neighboring group participation of an oxazolidinone in one case and an unexpected regiochemical outcome in another. The approach developed affords the C19-C35 substructure in 18 steps overall from ethyl acetoacetate and in adequate quantities (10% overall yield) to support the projected total synthesis.
• A stereocontrolled synthesis of a C19-C32 / C17-C30 Segment for swinholide A and misakinolide A, Cytotoxic dimeric macrolides from theonella swinhoei.
  作者：Ian Paterson、John G. Cumming

  DOI：10.1016/s0040-4039(00)78876-9

  日期：1992.5

  The C19-C32/C-17-C30 segment (-)-5 of swinholide A/misakinolide A was prepared in 15 steps (6% yield) from (+/-)-13. Key steps include the Sharpless epoxidation, 13 --> 14, the acetal allylation, 12 --> 16, the anti aldol, 17 + 11 --> 9, and the alkene hydroboration, 19 --> 20.
• Structure–activity relationship studies on an antitumor marine macrolide using aplyronine a–swinholide A hybrid
  作者：Takayuki Ohyoshi、Atsuhiro Takano、Imari Kikuchi、Tomotaka Ogura、Mayu Namiki、Yuto Miyazaki、Takahiro Hirano、Shota Konishi、Yuta Ebihara、Koichi Takeno、Ichiro Hayakawa、Hideo Kigoshi

  DOI：10.1039/d2ob00118g

  日期：——

  An aplyronine A–swinholide A hybrid, consisting of the macrolactone part of aplyronine A and the side chain part of swinholide A, was designed, synthesized, and biologically evaluated. This hybrid induced protein–protein interactions between two major cytoskeletal proteins actin and tubulin in the same manner as aplyronine A, and exhibited potent cytotoxicity and actin-depolymerizing activity. The

  设计、合成和生物学评估了由 alyronine A 的大环内酯部分和 swinholide A 的侧链部分组成的 alyronine A-swinholide A 杂化物。这种杂合体以与 alyronine A 相同的方式诱导两种主要细胞骨架蛋白肌动蛋白和微管蛋白之间的蛋白质相互作用，并表现出强大的细胞毒性和肌动蛋白解聚活性。N、N、O中甲氧基的重要性-三甲基丝氨酸酯通过使用杂合类似物的氨基酸部分的构效关系研究得到澄清。此外，比较 alyronine A 和 swinholide A 的侧链类似物的肌动蛋白解聚活性表明，swinholide A 的侧链类似物的肌动蛋白解聚活性比 alyronine A 弱得多。