O',O',O',O'-tetraacetylvincosamide | 52484-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: O',O',O',O'-tetraacetylvincosamide
• 英文别名: vincoside lactam tetraacetate；17β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-16α-vinyl-(3β,15β)-18-oxa-yohimb-19-en-21-one；(16R,17S)-17,18-epoxy-17-(tetra-O-acetyl-β-D-glucopyranosyloxy)-16-vinyl-(3β,15βH)-19-nor-coryn-18(20)-en-21-one；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1R,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 52484-98-7
• 化学式: C₃₄H₃₈N₂O₁₂
• 分子量: 666.682
• InChiKey: DXYRZNXJTNLWLT-GLYBQKEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O',O',O',O'-tetraacetylvincosamide 在 palladium diacetate 六甲基磷酰三胺 、 1,1'-双(二苯基膦)二茂铁 、 sodium periodate 、 甲酸 、 sodium methylate 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 106.5h， 生成 1-methoxy-4-vinyl-1,12-dihydro-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-13-one
  参考文献：
  名称：

  Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

  摘要：

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01196-1
• 作为产物：
  描述：

  色胺 在 吡啶 、 sodium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 O',O',O',O'-tetraacetylvincosamide
  参考文献：
  名称：

  Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

  摘要：

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01196-1

文献信息

• Configurative Correlation and Conformational Analysis of Strictosidine and Vincoside Derivatives
  作者：Ágnes Patthy-Lukáts、Ákos Kocsis、László F. Szabó、B. Podányi

  DOI：10.1021/np990150r

  日期：1999.11.1

  On the basis of the configuration of C-15 of the secologanin unit, using detailed NMR analysis, the configuration of C-3, the solution conformation around C-14, and the glucosidic bridge, as well as those of the dihydropyran and tetrahydropyridine rings, were determined in the vincosamide and strictosamide derivatives 4b and 5b. The stereochemical analysis was extended by chemical correlation to the

  根据次茄子苷元单元C-15的构型，使用详细的NMR分析，C-3的构型，C-14周围的溶液构象和糖苷桥以及二氢吡喃和四氢吡啶环的构象，是在vincosamide和strictosamide衍生物4b和5b中测定的。通过化学相关性将立体化学分析扩展至4-苄基丁糖苷和长春苷衍生物3c和3d。提出了实验证明来解释乙酰化的严格酰胺衍生物的“异常”化学位移。
• Bioinspired Divergent Oxidative Cyclization from Strictosidine and Vincoside Derivatives: Second‐Generation Total Synthesis of (−)‐Cymoside and Access to an Original Hexacyclic‐Fused Furo[3,2‐ <i>b</i> ]indoline
  作者：Yingchao Dou、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1002/chem.202003758

  日期：2020.12.18

  The second‐generation synthesis of (−)‐cymoside as well as the formation of a new hexacyclic‐fused furo[3,2‐b]indoline framework is reported. After a Pictet–Spengler condensation between secologanin tetraacetate and tryptamine, the course of the cyclization of the 7‐hydroxyindolenine intermediate, generated by oxidation with an oxaziridine, depended on the stereochemistry of the 3‐position. The 3‐(S)‐strictosidine

  据报道，（-）-cymoside的第二代合成以及新的六环融合呋喃[3,2- b ]二氢吲哚骨架的形成。仲硫代己宁四乙酸盐与色胺之间发生Pictet-Spengler缩合反应后，由恶唑烷氧化产生的7-羟基吲哚中间体中间环化的过程取决于3-位的立体化学。的3 - （小号）-strictosidine立体化学通过与C16-C17烯醇醚分子内偶合有效地传送cymoside的支架，而3 - （[R ）立体化学-vincoside朝向与C18-C19末端烯烃并形成反应意外的笼状化合物。
• Biogenetically patterned synthesis of camptothecin and 20-deoxycamptothecin
  作者：Richard T Brown、Liu Jianli、Cid A.M Santos

  DOI：10.1016/s0040-4039(99)02210-8

  日期：2000.2

  A biogenetically patterned synthetic route to the monoterpenoid quinoline alkaloids 20-deoxycamptothecin and (±)-camptothecin from secologanin and tryptamine via vincoside/strictosidine lactams has now been realized, and hence afforded likely biosynthetic intermediates for testing in vivo.

  现在已经实现了通过泛醇苷/缩尿嘧啶内酰胺从secologanin和色胺中获得从单萜类化合物到20脱氧喜树碱和（±）-喜树碱的单萜类喹啉生物碱的生物遗传模式合成途径，因此提供了可能的生物合成中间体用于体内测试。
• Isolation and partial synthesis of 3(R)- and 3(S)-deoxypumiloside; structural revision of the key metabolite from the camptothecin producing plant, Ophiorrhiza pumila
  作者：Mariko Kitajima、Seiji Masumoto、Hiromitsu Takayama、Norio Aimi

  DOI：10.1016/s0040-4039(97)00858-7

  日期：1997.6

  the C-3 epimeric pair of 3(R)- and 3(S)-deoxypumiloside were found in Ophiorrhiza pumila (Rubiaceae), a source plant of camptothecinoid metabolites. These structures were confirmed by spectroscopic analysis and partial stereoselective syntheses. The configuration at C-3 of the previously reported “deoxypumiloside” is revised to 3(R) from 3(S).

  在喜树碱代谢物的来源植物Ophiorrhiza pumila（Rubiaceae）中发现了C-3的3（R）-和3（S）-脱氧普米洛甙对映体对。这些结构通过光谱分析和部分立体选择性合成得到证实。先前报道的“脱氧油苷”在C-3处的构型从3（S）修订为3（R）。
• Studies on plants containing indole alkaloids. VIII. Indole alkaloid glycosides and other constituents of the leaves of Uncaria rhynchophylla Miq.
  作者：NORIO AIMI、TOSHIAKI SHITO、KAYOKO FUKUSHIMA、YUMIKO ITAI、CHIFUMI AOYAMA、KEIKO KUNISAWA、SHINICHIRO SAKAI、JOJU HAGINIWA、KAZUO YAMASAKI

  DOI：10.1248/cpb.30.4046

  日期：——

  A new glycoindole alkaloid, rhynchophine, was isolated from the leaves of Uncaria rhynchophylla MIQ. and its structure was elucidated as 6'-feruloyl vincoside lactam (IV). A partial synthesis was achieved by the use of vincoside lactam as the starting material. Five known compounds were also newly isolated from the same plant, namely, vallesiachotamine, vincoside lactam, strictosamide, hyperin and trifolin.

  从钩藤（Uncaria rhynchophylla MIQ.）的叶子中分离出一种新的糖茚生物碱——钩藤碱（rhynchophine），并确定其结构为6'-阿魏酰长春质内酰胺（IV）。以长春质内酰胺为起始原料，实现了部分合成。此外，还从同一植物中分离出五种已知化合物，分别是瓦勒西亚胺（vallesiachotamine）、长春质内酰胺（vincoside lactam）、斯特里科酰胺（strictosamide）、金丝桃素（hyperin）和三叶草素（trifolin）。