1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione | 143658-69-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-hydroxysuccinimide；1-[(2,3,4,6-tetra-O-acetyl-β-D-glucosyl)oxy]-2,5-pyrrolidinedione；2,3,4,6-tetra-O-acetyl-O-β-D-glucopyranosyl-N-oxysuccinimide；N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)succinimide；1-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyloxy)-pyrrolidine-2,5-dione；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,5-dioxopyrrolidin-1-yl)oxyoxan-2-yl]methyl acetate
• CAS: 143658-69-9
• 化学式: C₁₈H₂₃NO₁₂
• 分子量: 445.38
• InChiKey: FXFOHFDUFLAHFG-CUWKQTPXSA-N

物化性质

• 沸点：
  511.7±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione 在 盐酸 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 74.0h， 生成 O-(β-D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-d-glucopyranosylhydroxylamine—new CN ligands stable towards hydrolysis

  摘要：

  A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00451-7
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 氢溴酸 、 四丁基硫酸氢铵 、 乙酸酐 、 sodium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages

  摘要：

  We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4-17 mu M), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having beta-lactosides and having beta-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells. (c) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2018.02.001

文献信息

• Design and synthesis of cluster neoglycoconjugates based on D-glucose
  作者：N. A. Kurochkina、U. A. Budanova、Yu. L. Sebyakin

  DOI：10.1134/s1070428014100157

  日期：2014.10

  tetravalent neoglycoconjugates with different structures of the hydrophobic fragment and D-glucose fragment as branching core. The syntheses have been accomplished by preparation of blocks with terminal C≡C triple bonds and hydrophobic fragment and hydrophilic component (lactose derivative), followed by their conjugation.

  已经开发出合成方法来合成具有疏水片段和D-葡萄糖片段的不同结构作为分支核心的四价新糖缀合物。合成是通过制备具有末端C≡C三键，疏水性片段和亲水性成分（乳糖衍生物）的嵌段，然后进行缀合来完成的。
• Multivalent presentation of carbohydrates by 3₁₄-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition
  作者：Nitin J. Pawar、Ulf Diederichsen、Dilip. D. Dhavale

  DOI：10.1039/c5ob01673h

  日期：——

  A tetrameric glycoconjugate template, SSFT 1, was coupled with a variety of six aminooxy sugars to achieve multivalent glycoconjugates 2–7.

  一个四聚糖结合物模板，SSFT 1，与多种六个氨氧基糖偶联，以实现多价糖结合物2-7。
• Stereoselective phase transfer catalyzed syntheses of glycosyloxysuccinimides and their transformations into glycoprobes
  作者：Suoding Cao、François D. Tropper、René Roy

  DOI：10.1016/0040-4020(95)00325-3

  日期：1995.6

  Glycosyloxysuccinimides of D-galactose, D-glucose, N-acetyl-D-glucosamine, lactose, maltose (7–11) and sialic acid (13) were prepared from their glycosyl halides under PTC conditions. Ring opening of the succinimide moieties occurred with sodium hydroxide or methoxide to provide extended aglycons, while treatment of 8 with hydrazine afforded O-galactopyranosylhydroxylamine 17. Treatment of 9 with

  D-半乳糖，D-葡萄糖，N-乙酰基-D-葡萄糖胺，乳糖，麦芽糖（7-11）和唾液酸（13）的糖基氧基琥珀酰亚胺是在PTC条件下由它们的糖基卤化物制备的。琥珀酰亚胺部分的开环发生与氢氧化钠或甲醇盐，以提供延长的糖苷配基，而用肼处理8提供O- galactopyranosylhydroxylamine 17。用三（2-氨基乙基）胺处理9得到二价簇20，其在用异硫氰酸荧光素进一步处理后提供二价糖探针21。
• Design and synthesis of an octavalent bolaamphiphile with terminal lactose residues
  作者：I. S. Shchelik、Yu. L. Sebyakin

  DOI：10.1134/s1070428015120088

  日期：2015.12

  The synthesis of an octavalent bolaamphiphile with D-glucose moiety as branching unit has been designed and accomplished via 1,3-dipolar cycloaddition of bis(tetra-O-propargylglucoside) and 8 equiv of 2-azidoethyl beta-D-lactoside.
• Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy
  作者：Bernd L. Sorg、William E. Hull、Hans-Christian Kliem、Walter Mier、Manfred Wiessler

  DOI：10.1016/j.carres.2004.11.024

  日期：2005.2

  Tumor targeting of glycoconjugated antineoplastic agents is a strategy currently under investigation for cancer chemotherapy. We have synthesized the glucosides and galactosides of the clinically established drug hydroxyurea and of mesylglycol, the reactive moiety of the anticancer drug busulfan. Glycosides of hydroxyurea were obtained by carbamoylation of hydroxylamine glycosides. The glycosides of mesylglycol were synthesized by mesylation of protected glycol glycosides. All compounds were characterized by detailed H-1 and C-13 NMR analysis. (C) 2004 Published by Elsevier Ltd.