(3'S,4'S,4'aR,8'aR)-4'-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene] | 474055-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S,4'S,4'aR,8'aR)-4'-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene]
• CAS: 474055-48-6
• 化学式: C₂₆H₃₈O₄
• 分子量: 414.585
• InChiKey: PZLSEGWILHENIY-WQPRPRDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'S,4'S,4'aR,8'aR)-4'-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene] 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (+)-{5-[2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate}
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e
• 作为产物：
  描述：

  3-糠醛 在 Grubbs catalyst first generation 、 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 4-二甲氨基吡啶 、 lithium hydroxide 、 氨 、 氢气 、 lithium 、 sodium hydride 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三乙胺 、 N,N'-二异丙基碳二亚胺 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， -78.0~75.0 ℃ 、303.98 kPa 条件下， 反应 194.5h， 生成 (3'S,4'S,4'aR,8'aR)-4'-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-3',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,4a,5,6,7-hexahydro-1H-naphthalene]
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e

文献信息

• Total Synthesis of (+)-Cacospongionolide B
  作者：Susumu Kobayashi、Motoko Oshida、Misaki Ono、Atsuo Nakazaki

  DOI：10.3987/com-09-s(s)17

  日期：——

  Total synthesis of (+)-cacospongionolide B was achieved. The synthesis involved highly stereoselective C-glycosidation of a glycal derived from D-arabinose with 3-furyl boronic acid in the presence of a palladium catalyst and B-alkyl Suzuki-Miyaura coupling of in situ generated alkylborane prepared by the reaction of vinyl trans-decalin with alkenyl triflate.

  实现了(+)-cacospongionolide B的全合成。该合成涉及在钯催化剂和 B-烷基 Suzuki-Miyaura 偶联的情况下，由 D-阿拉伯糖衍生的糖苷与 3-呋喃基硼酸的高度立体选择性 C-糖苷化反应，通过乙烯基反式反应制备的烷基硼烷萘烷与三氟甲磺酸烯基酯。
• Total Syntheses of (+)- and (−)-Cacospongionolide B:  New Insight into Structural Requirements for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Marc L. Snapper

  DOI：10.1021/ja026899x

  日期：2002.10.1

  The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.
• Conformationally Restricted (+)-Cacospongionolide B Analogues. Influence on Secretory Phospholipase A₂ Inhibition
  作者：Ryan P. Murelli、Atwood K. Cheung、Marc L. Snapper

  DOI：10.1021/jo061407a

  日期：2007.3.1

  A new approach to (+)-cacospongionolide was developed to access conformationally restricted variants of the natural product. The flexible aliphatic region between the decalin and side chain portion of the natural product was replaced with alkenyl and alkynyl linkers to probe the influence of structural rigidity in the inhibition of secretary phospholipase A(2) (sPLA(2)). It was found that when the aliphatic section is replaced with a Z-olefin or an alkyne, sPLA(2) inhibitory activity suffered relative to the natural product; however, an E-olefin-containing analogue led to an enhanced activity. These results suggest that preferred sPLA(2) binding conformation of the natural product is similar to the geometry of the E-olefin-containing analogue.
• Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Ryan Murelli、Marc L. Snapper

  DOI：10.1021/jo049285e

  日期：2004.8.1

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.