2-propynyl-2,3,4,6-tetra-O-acetyl-α-L-(-)-mannopyranoside | 1194524-95-2

• 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: 2-propynyl-2,3,4,6-tetra-O-acetyl-α-L-(-)-mannopyranoside
• 英文别名: 2-propynyl 2,3,4,6-tetra-O-acetyl-α-L-mannopyranoside
• CAS: 1194524-95-2
• 化学式: C₁₇H₂₂O₁₀
• 分子量: 386.356
• InChiKey: HKGFUJKLPCRVFW-FIDHJVLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-propynyl-2,3,4,6-tetra-O-acetyl-α-L-(-)-mannopyranoside 、 5,5'''-diiodo-3,3'''-didodecyl-[2,2';5',2'';5'',2''']quaterthiophene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 反应 16.0h， 以62%的产率得到3-[3,3'''-didodecyl-5'''-[3-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyloxy)-1-propyn-1-yl][2,2':5',2'':5'',2'''-quaterthien]-5-yl]-2-propyn-1-yl-α-L-mannopyranose tetraacetate
  参考文献：
  名称：

  Self-Assembling Carbohydrate-Functionalized Oligothiophenes

  摘要：

  Carbohydrate-functionalized oligothiophenes have been synthesized applying mild Sonogashira cross-coupling conditions. In an aqueous environment the amphiphilic hybrids self-assemble into chiral superstructures as a result of multiple hydrogen bond interactions and the helicity of the aggregates is controllable by the configuration of the carbohydrate unit. By means of atomic force microscopy highly ordered layer arrangements on substrates were characterized.

  DOI：

  10.1021/ol9022694
• 作为产物：
  描述：

  2-丙炔-1-醇 、 1,2,3,4,6-penta-O-acetyl-α,β-L-mannopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2-propynyl-2,3,4,6-tetra-O-acetyl-α-L-(-)-mannopyranoside 、 2-propynyl 2,3,4,6-tetra-O-acetyl-β-L-mannopyranoside
  参考文献：
  名称：

  Self-Assembling Carbohydrate-Functionalized Oligothiophenes

  摘要：

  Carbohydrate-functionalized oligothiophenes have been synthesized applying mild Sonogashira cross-coupling conditions. In an aqueous environment the amphiphilic hybrids self-assemble into chiral superstructures as a result of multiple hydrogen bond interactions and the helicity of the aggregates is controllable by the configuration of the carbohydrate unit. By means of atomic force microscopy highly ordered layer arrangements on substrates were characterized.

  DOI：

  10.1021/ol9022694

文献信息

• Sugar-Modified Foldamers as Conformationally Defined and Biologically Distinct Glycopeptide Mimics
  作者：Aloysius Siriwardena、Kiran Kumar Pulukuri、Pancham S. Kandiyal、Saumya Roy、Omprakash Bande、Subhash Ghosh、José Manuel Garcia Fernández、Fernando Ariel Martin、Jean-Marc Ghigo、Christophe Beloin、Keigo Ito、Robert J. Woods、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1002/anie.201304239

  日期：2013.9.23

  To fold or not to fold? It is shown that attached sugars play a defining role in the conformations adopted by a pair of novel SAA‐derived foldamers in water and that these differences are reflected in the contrasting interactions of these glycofoldamers with various biological targets. C green, O red, N blue, H gray; yellow oval=mannose.

  折叠还是不折叠？结果表明，附着的糖在水中一对新型 SAA 衍生折叠体所采用的构象中起着决定性作用，并且这些差异反映在这些糖折叠体与各种生物靶标的对比相互作用中。C绿、O红、N蓝、H灰；黄色椭圆形=甘露糖。
• Self-organizing carbohydrate-oligothiophene-hybrids for eukaryotic membrane-labelling
  作者：Sylvia Schmid、E. Marion Schneider、Eduard Brier、Peter Bäuerle

  DOI：10.1039/c4tb01472c

  日期：——

  Self-assembling d-(+) and l-(−) mannose-functionalized oligothiophene hybrids were synthesized via Sonogashira cross-coupling reaction. The hybrids are taken up into live myeloid cells and offer an ideal platform for imaging of artificial and cellular membranes.

  通过Sonogashira交叉偶联反应合成了自组装d-(+)和l-(−)甘露糖功能化寡噻吩杂化物。这些杂化物被活的髓系细胞吞噬，并提供了一个理想的平台，用于人工和细胞膜成像。