peracetylated α-maltosyl trichloroacetimidate | 92052-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: peracetylated α-maltosyl trichloroacetimidate
• 英文别名: 2,2',3,3',4',6,6'-hepta-O-acetyl-α-D-maltosyl trichloroacetimidate；2,3,4,6-tetra-O-acetyl-1-O-trichloroacetimidoyl-α-D-maltopyranose；2,3,6,2,3′,4′,6′-hepta-O-acetyl-α-maltosyl trichloroacetimidate；2,2′,3,3′,4,4′,6,6′-hepta-O-acetyl-α-D-maltosyl trichloroacetimidate；1-alpha-trichloroacetimidoyl-2,3,6-O-triacetylglucopyranosyl-4-alpha-(2′,3′,4',6'-O-tetraacetyl)glucopyranoside；2,3,6,2’,3’,4’,6’-hepta-O-acetyl-α-maltosyl trichloroacetimidate；2,2',3,3',4,4',6,6'-octa-O-acetyl-α-D-maltopyranosyl trichloroacetimidate；2,3,6,2',3',4',6'-hepta-O-acetyl-α-maltosyl trichloroacetimidate；heptaacetyl-α-D-dimaltosyloxytrichloroacetonitrile；Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 92052-38-5
• 化学式: C₂₈H₃₆Cl₃NO₁₈
• 分子量: 780.949
• InChiKey: QUJSSIATSJUBGC-PCIRLDFKSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  690.0±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  peracetylated α-maltosyl trichloroacetimidate 在 吡啶 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Large Oligosaccharide-Based Glycodendrimers Synthetic Carbohydrate Dendrimers, Part 9: for Part 8, see: W. B. Turnbull, A. R. Pease, J. F. Stoddart, ChemBioChem 2000, 1, 70–74.

  摘要：

  Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB, monomers are based on a maltosylbeta(1 --> 6)galactose structure, which has been modified to include two methylamino groups at the primary positions of the glucosyl residues. Reductive alkylation of the secondary amino groups, with the innate formyl function of a second oligosaccharide monomer, allows for the chemoselective construction of dendritic wedges. while employing a minimal number of protecting groups. The first-generation dendron can be coupled either to another AB? monomer, to give a second-generation dendron, or to a tris[2-(methylamino)ethyl] a mine-based core moiety, to provide a carbohydrate-based dendrimer. Alternating alpha- and beta-glucosyl residues in the monomers and dendrons, simplifies H-1 NMR spectra as a consequence of spreading out the anomeric proton signals. Monomers and dendrons were characterized by extensive one- and two-dimensional NMR spectroscopy in addition to FAB, electrospray, and MALDI-TOF mass spectrometry. Molecular dynamics simulations revealed similar conformations in the dendrons as in the isolated trisaccharide repeating units.

  DOI：

  10.1002/1521-3765(20020703)8:13<2988::aid-chem2988>3.0.co;2-2
• 作为产物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 在 碳酸氢铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 peracetylated α-maltosyl trichloroacetimidate
  参考文献：
  名称：

  带有饱和，不饱和和甲基支链脂肪酸和脂肪醇链的糖基二烷基甘油和二酰基甘油的合成和介晶性质。第一部分：合成。

  摘要：

  合成了在尾部带有饱和，不饱和或手性甲基支链的糖基二烷基和二酰基甘油，以及二糖和三糖碳水化合物头基。使用标准程序制备离析物和糖脂：使用三氯乙亚胺酸酯程序制备长链化合物，使用β-过乙酸酯和三氟化硼醚化物进行糖基化成功制备了中等烷基链长的脂质。根据公开的方法，通过多步合成提供了酯的制备。因此，在几个合成步骤中以高收率合成了几种脂质。不饱和或甲基支链的引入导致环境温度下的液晶性，因为这些化合物将用作生物系统的模型化合物。这些化合物的生物物理特性将在随后的论文中报道。

  DOI：

  10.1016/j.chemphyslip.2005.01.004

文献信息

• Maltose and Maltotriose Derivatives as Potential Inhibitors of the Maltose-Binding Protein
  作者：Heinz Malik、Winfried Boos、Richard R. Schmidt

  DOI：10.1002/ejoc.200701139

  日期：2008.4

  Inhibition of substrate binding to maltose-binding protein (MBP) was investigated with structurally modified maltose and maltotriose derivatives that were designed based on the X-ray analysis of maltose and maltotriose bound to MBP. In maltose, positions 1a, 2a, 2b, 4b and 6b were modified (compounds 1–3, 18a, b, 28a–c, 39 and 44) of which only the trivalent maltose derivatives 39 and 44 exhibited high affinity

  使用结构修饰的麦芽糖和麦芽三糖衍生物研究底物与麦芽糖结合蛋白 (MBP) 结合的抑制作用，这些衍生物是基于与 MBP 结合的麦芽糖和麦芽三糖的 X 射线分析而设计的。在麦芽糖中，1a、2a、2b、4b 和 6b 位被修饰（化合物 1-3、18a、b、28a-c、39 和 44），其中只有三价麦芽糖衍生物 39 和 44 对 MBP 表现出高亲和力。在位置 6a 和 6c（化合物 45-51）进行麦芽三糖修饰。具有 6α-O-丙基的化合物 50 和其中 6c-羟基被溴化物取代的化合物 51 对 MBP 的亲和力高于母体麦芽三糖。因此，结构上完全不同的化合物 39、50 和 51 是进一步研究的重要先导化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,
• Click Chemistry: An Efficient Synthesis of Heterocycles Substituted with Steroids, Saponins, and Digitalis Analogues
  作者：Márcio Paixão、Anna Deobald、Leandro Camargo、Diego Alves、Julio Zukerman-Schpector、Arlene Corrêa

  DOI：10.1055/s-0031-1289606

  日期：2011.12

  partner allowed the synthesis of a privileged class of natural product analogues. The versatility of this protocol makes this chemistry a useful attractive approach for the synthesis of target molecules. click chemistry - 1,2,3-triazole - sugars - steroids - saponins - digitalis

  铜催化的叠氮化物-炔烃环加成反应（CuAAC）已用于高产，高产的含1,2,3-三唑类固醇的构建。炔丙基糖苷和甾类叠氮化物作为反应伴侣的组合允许合成一类特权的天然产物类似物。该方案的多功能性使该化学成为合成目标分子的有用的有吸引力的方法。 点击化学-1,2,3-三唑-糖-类固醇-皂苷-洋地黄
• Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
  作者：Mohamed Ramadan El Sayed Aly、Hosam Ali Saad、Shams Hashim Abdel-Hafez

  DOI：10.3762/bjoc.11.208

  日期：——

  3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate 6c showed the best antimicrobial activity, while the lactoside conjugate 27 showed the best cytotoxic effect in vitro.

  3β-氮杂胆甾-5-烯（3）和（3β）-3-(丙-2-炔-1-氧基)胆甾-5-烯（10）被制备为底物，以合成各种三基团药效团结合物通过CuAAC。基本上，这些结合物包括胆固醇和1,2,3-三唑基团，而第三个药效团则是香豆素、疏水残基或碳水化合物标记中的一个。这些化合物以良好的产率成功制备，并通过NMR、MS和IR光谱技术进行表征。香豆素结合物6c显示出最佳的抗微生物活性，而乳糖苷结合物27在体外显示出最佳的细胞毒作用。
• Ring-opening polymerization of new 3-O-branched 1, 6-anhydro glucopyranose di- and trisaccharide monomers
  作者：Chaolumen Bai、Davaanyam Budragchaa、Takashi Yoshida

  DOI：10.1016/j.carres.2017.04.017

  日期：2017.6

  6-anhydro disaccharide monomers were polymerized. However, the polymerizability was lower than that of the 4-O-branched disaccharide monomers reported previously, and the trisaccharide monomer was not polymerizable, probably due to the steric hindrance of the branched bulky mono and disaccharide units at the 3-O position in 1, 6-anhydro glucopyranose. Debenzylation of the resulting polymers gave 3-O-gluco-

  新的3-O支链1、6-脱水吡喃葡萄糖二糖单体，1，6-脱水-2、4-二-O-苄基-3-O-（2'，3'，4'，6'-四- O-苄基-α-D-甘露吡喃糖基）-（LGM 6）和-葡萄糖吡喃糖基）-β-D-吡喃葡萄糖（LGG 7）和三糖单体1、6-脱水-2、4-二-O-苄基-3-O-α-（2'，3'，6'，2''，3''，4''，6''-庚基-O-苄基-α-D-麦芽吡喃糖基）-β-D-吡喃葡萄糖（LGMAL 8 ）合成和聚合。发现3-O-支链的1，6-脱水二糖单体已聚合。然而，可聚合性低于先前报道的4-O-支化二糖单体，并且三糖单体不可聚合，这可能是由于1中3-O位置支链的庞大单糖和二糖单元的空间位阻，6-脱水吡喃葡萄糖。所得聚合物的脱苄基作用以中等收率得到了3-O-葡萄糖基和甘露吡喃糖苷（1→6）-α-D-吡喃葡聚糖。这些结果是3-O-支链的1,6-脱水脱水吡喃葡萄糖二糖单体聚合生成3-O-支链的多糖的首次报道。
• Glycosylation of a Ketone with an <i>O</i>-Glycosyl Trichloroacetimidate Provides an Enol Glycoside
  作者：Xianglai Liu、Sumei Ren、Qi Gao、Chun Hu、Yingxia Li、Ning Ding

  DOI：10.1021/acs.orglett.8b02126

  日期：2018.9.7

  An enol-type glycosylation reaction has been investigated. Enol glycosides can be obtained from the reaction between O-glycosyl trichloroacetimidates and the corresponding ketones promoted by an acid. The enol glycosides derived from cyclic ketones can be afforded efficiently and isolated in good yield, while those from acyclic ketones are prepared in low conversion or are too labile for isolation

  已经研究了烯醇型糖基化反应。烯醇糖苷可以从O-糖基三氯乙亚氨酸酯与相应的由酸促进的酮之间的反应中获得。可以有效地提供衍生自环状酮的烯醇糖苷并以高收率分离，而衍生自无环酮的烯醇糖苷转化率低或太不稳定而无法分离。对不同糖基供体类型的进一步研究表明，只有O-糖基三氯乙酰亚氨酸酯可以很好地用作烯醇糖基化的供体。