O',O',O',O'-tetraacetylstrictosamide | 23141-26-6

• 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'-tetraacetylstrictosamide
• 英文别名: strictosamine tetraacetate；strictosidine lactam tetraacetate；strictosamide tetraacetate；17β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-16α-vinyl-(15β)-18-oxa-yohimb-19-en-21-one；(16R,17S)-17,18-epoxy-17-(tetra-O-acetyl-β-D-glucopyranosyloxy)-16-vinyl-(15βH)-19-nor-coryn-18(20)-en-21-one；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1S,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: 23141-26-6
• 化学式: C₃₄H₃₈N₂O₁₂
• 分子量: 666.682
• InChiKey: DXYRZNXJTNLWLT-KCOMPZLBSA-N

物化性质

• 沸点：
  791.8±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

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'-tetraacetylstrictosamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以0.14 g的产率得到O',O',O',O'-tetraacetyl-18,19-dihydrostrictosamide
  参考文献：
  名称：

  严格的苷和长春苷衍生物的构型相关性和构象分析

  摘要：

  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。

  DOI：

  10.1021/np990150r
• 作为产物：
  描述：

  色胺盐酸盐 在 吡啶 、 色胺 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 8.0h， 生成 O',O',O',O'-tetraacetylstrictosamide
  参考文献：
  名称：

  严格的苷和长春苷衍生物的构型相关性和构象分析

  摘要：

  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。

  DOI：

  10.1021/np990150r

文献信息

• 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）。
• Deeper Insights into the Stereostructure of Strictosamide Tetraacetate and Methylisoalangiside Tetraacetate the Key Reference Molecules in Monoterpenoid Indole- and Isoquinoline Glucoalkaloids.
  作者：Hiromitsu TAKAYAMA、Osamu OHMORI、Sanan SUBHADHIRASAKUL、Mariko KITAJIMA、Norio AIMI

  DOI：10.1248/cpb.45.1231

  日期：——

  The highly shifted acetyl NMR signal of strictosamide tetraacetate, one of the most important reference molecules in the glucoindole alkaloid fields, is that on C2' of the glucose moiety. The signal that behaves similarly in methylisoalangiside tetraacetate was also confirmed to be that on C2'.

  严格苷酰胺四乙酸酯是葡萄糖吲哚生物碱领域最重要的参考分子之一，其高度偏移的乙酰 NMR 信号是葡萄糖分子 C2' 上的信号。在甲基异柳酰胺四乙酸酯中表现类似的信号也被证实是 C2'上的信号。
• Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia
  作者：Atsuko Itoh、Takao Tanahashi、Naotaka Nagakura、Toyoyuki Nishi

  DOI：10.1016/s0031-9422(02)00541-1

  日期：2003.2

  From the dried roots of Neonauclea sessilifolia, two new chromone-secoiridoid glycosides, sessilifoside and 7"-O-beta-D-glucopyranosylsessilifoside, and three novel indole alkaloid glycosides, neonaucleosides A, B, and C, were isolated along with the main known glycosides, 5-hydroxy-2-methylchromone-7-O-beta-D-apiofuranosyl-(l --> 6)-beta-D-glucopyranoside, sweroside, loganin, grandifloroside, and quinovic acid 3beta-O-beta-D-quinovopyranoside-28-O-beta-D-glucopyranoside. The structures of these new glycosides were determined by spectroscopic and chemical means. Neonaucleoside A and its C-3 epimer were prepared from secologanin and tryptamine. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila
  作者：Mariko Kitajima、Satoshi Yoshida、Kyoko Yamagata、Mio Nakamura、Hiromitsu Takayama、Kazuki Saito、Hiroko Seki、Norio Aimi

  DOI：10.1016/s0040-4020(02)01196-1

  日期：2002.11

  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.
• Arbain, Dayar; Putra, Deddi Prima; Sargent, Melvyn V., Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 977 - 985
  作者：Arbain, Dayar、Putra, Deddi Prima、Sargent, Melvyn V.

  DOI：——

  日期：——