methyl Z-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate | 294664-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl Z-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate
• 英文别名: [(2R,3S,4S,5S)-4-benzamido-3-benzoyloxy-5-[(Z)-3-methoxy-3-oxoprop-1-enyl]oxolan-2-yl]methyl benzoate
• CAS: 294664-40-7
• 化学式: C₃₀H₂₇NO₈
• 分子量: 529.546
• InChiKey: JNDJXDMSNNXPQM-VTYGWQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl Z-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate 在 氯 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 2.0h， 生成 4-((2S,3S,4S,5R)-3-Benzoylamino-4-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  从d-葡萄糖立体定向合成两种新型细胞毒性吡唑C-核苷

  摘要：

  通过使用2，5-脱水-d-葡萄糖乙烯乙缩醛衍生物1作为发散中间体，已经从d-葡萄糖开始实现了两个新颖的吡唑C-核苷12和21的多步立体有择合成。所述Ç核苷12被证明是的N2a细胞和BHK 21肿瘤细胞系的体外生长的适度抑制，而21显示出适度的细胞毒性活性仅仅针对N2a细胞。

  DOI：

  10.1016/s0040-4039(00)00894-7
• 作为产物：
  描述：

  Potassium benzoate 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 氯仿 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 313.0h， 生成 methyl Z-4,7-anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-D-allo-oct-2-enoate
  参考文献：
  名称：

  从d-葡萄糖立体定向合成两种新型细胞毒性吡唑C-核苷

  摘要：

  通过使用2，5-脱水-d-葡萄糖乙烯乙缩醛衍生物1作为发散中间体，已经从d-葡萄糖开始实现了两个新颖的吡唑C-核苷12和21的多步立体有择合成。所述Ç核苷12被证明是的N2a细胞和BHK 21肿瘤细胞系的体外生长的适度抑制，而21显示出适度的细胞毒性活性仅仅针对N2a细胞。

  DOI：

  10.1016/s0040-4039(00)00894-7

文献信息

• C–H⋅sO hydrogen bond networks in E- and Z-unsaturated esters of C-glycosides
  作者：Agneš Kapor、Dieter Zobel、Marianna Strümpel、Ljilja Torović、Mirjana Popsavin

  DOI：10.1007/s10870-005-3479-7

  日期：2005.9

  Methyl E(Z)-4,7 anhydro-5-benzamido-6,8-di-O-benzoyl-2,3,5-trideoxy-d-allo-oct-2-enoate have been synthesized like intermediates and isolated as single crystals during the synthesis of pyrazole-related C nucleosides as synthetic product with cytotoxic activity.1 Crystal structures of E(Z) isomers were determined by X-ray analysis. E isomer crystallizes in the triclinic crystal system, space group P1, a = 5.319(1) Å, b = 10.758(2) Å, c = 12.229(2) Å, α = 72.38(2)∘, β = 89.97(2)∘, γ = 87.07(2)∘, D x = 1.320 Mgm−3 and Z isomer in the orthorhombic crystal system, space group P212121, a = 5.1297(13) Å, b = 19.667(5) Å, c = 25.871(6) Å, D x = 1.348 Mgm−3. The molecular structure was solved by direct method on the basis of 2609 and 2727 unique reflections recorded at the temperature 293 K (E-isomer) and 173 K (Z-isomer) up to the final R-factor 0.0378 and 0.0435, respectively. C–H⋅sO contact networks were analyzed and the correlation established between the existence of the weak C–H⋅sO hydrogen bonds and the melting point of the single crystals.

  甲基E(Z)-4,7脱水-5-苯甲酰胺基-6,8-二-O-苯甲酰基-2,3,5-三脱氧-D-别-2-辛烯酸酯作为中间体被合成，并在吡唑相关C核苷的合成过程中被分离为单晶，作为具有细胞毒性活性的合成产物。1 E(Z)异构体的晶体结构通过X射线分析确定。E异构体在三斜晶系中结晶，空间群P1，a = 5.319(1) Å，b = 10.758(2) Å，c = 12.229(2) Å，α = 72.38(2)∘，β = 89.97(2)∘，γ = 87.07(2)∘，D x = 1.320 Mgm−3，Z异构体在正交晶系中结晶，空间群P212121，a = 5.1297(13) Å，b = 19.667(5) Å，c = 25.871(6) Å，D x = 1.348 Mgm−3。分子结构通过直接
• Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties
  作者：Mirjana Popsavin、Ljilja Torović、Saša Spaić、Srdjan Stankov、Agneš Kapor、Zoran Tomić、Velimir Popsavin

  DOI：10.1016/s0040-4020(01)01126-7

  日期：2002.1

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereospecific synthesis of two novel cytotoxic pyrazole C-nucleosides from d-glucose
  作者：Mirjana Popsavin、Ljilja Torovic、Saša Spaic、Srdjan Stankov、Velimir Popsavin

  DOI：10.1016/s0040-4039(00)00894-7

  日期：2000.7

  A multistep stereospecific synthesis of two novel pyrazole C-nucleosides 12 and 21 has been achieved starting from d-glucose, by utilizing the 2,5-anhydro-d-glucose ethylene acetal derivative 1 as a divergent intermediate. The C-nucleoside 12 was shown to be a moderate inhibitor of the in vitro growth of N2a and BHK 21 tumor cell lines, whereas 21 showed a moderate cytotoxic activity only against N2a

  通过使用2，5-脱水-d-葡萄糖乙烯乙缩醛衍生物1作为发散中间体，已经从d-葡萄糖开始实现了两个新颖的吡唑C-核苷12和21的多步立体有择合成。所述Ç核苷12被证明是的N2a细胞和BHK 21肿瘤细胞系的体外生长的适度抑制，而21显示出适度的细胞毒性活性仅仅针对N2a细胞。