ethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 210223-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-6)Glc2Ac3Ac4Ac(b)-SEt；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-ethylsulfanyloxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 210223-74-8
• 化学式: C₂₈H₄₀O₁₇S
• 分子量: 680.681
• InChiKey: UYXLPJCOJSYRSR-HYSGBLIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到ethyl 1-thio-gentiobioside
  参考文献：
  名称：

  Trisaccharide synthesis by glycosyl transfer from p-nitrophenyl β-d-N-acetylgalactosaminide on to disaccharide acceptors catalysed by the β-N-acetylhexosaminidase from Aspergillus oryzae

  摘要：

  The beta-N-acetylhexosaminidase from Aspergillus oryzae catalysed the transfer of beta-D-N-acetylgalactosaminyl residues from p-nitrophenyl beta-D-N-acetylglucosaminide on to disaccharide accepters consisting of thioethyl glycosides of alpha-D-Glc-(1 --> 4)-beta-D-Glc, beta-D-Glc-(1 --> 4)-beta-D-Glc and beta-D-Glc-(1 --> 6)-beta-D-Glc. The principle of 'anomeric control' was exemplified by the results which showed that an alpha-linkage between the units of the acceptor favoured exclusively the formation of a new (1 --> 4)-linkage, whereas the beta-configuration in the acceptor led to a mixture of (1 --> 4)- and (1 --> 3)-linked products, as observed for simple glycosides of monosaccharide accepters. With the thioethyl beta-lactoside as acceptor, beta-D-Gal(1 --> 6)-beta-D-Gal-(1 --> 4)-beta-D-GlcSEt was formed, owing to the action of residual beta-D-galactosidase activity in the N-acetylhexosaminidase on the thioethyl beta-lactoside acting as both donor and acceptor. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10030-1
• 作为产物：
  描述：

  乙酸酐 、 ethyl 1-thio-gentiobioside 在 吡啶 作用下， 反应 12.0h， 生成 ethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  糖基硫亚氨酸盐在固相寡糖合成中的应用

  摘要：

  研究了两类稳定的硫代酰亚胺基衍生物，即S-苯并恶唑基（SBox）和S-噻唑啉基（STaz）糖苷，作为固相寡糖合成的糖基供体。已证明这些衍生物既适用于糖基受体结合的策略，也适用于糖基供体结合的策略，通常用于树脂支持的寡糖合成中。

  DOI：

  10.1021/jo701902f

文献信息

• Conformational properties of glucosyl-thioglucosides and their S-oxides in solution
  作者：Carlos A. Sanhueza、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.tetasy.2013.03.020

  日期：2013.5

  aglycone, the solvent and, in the S-oxides, on the absolute configuration of the sulfur atom. The results for the thio-disaccharides showed the strong influence of the solvent polarity on the conformational preferences of the interglycosidic bond. In polar solvents, the magnitudes of the rotamer populations, Pgg and Pgt, remained practically constant through the series, while in non-polar solvents a clear

  通过核磁共振和圆二色性对一系列烷基葡糖基-β-（1→6）-硫代葡糖苷及其S-氧化物的立体化学研究显示，硫代葡糖苷键（环I）周围的种群以及糖苷间键ω取决于糖苷配基，溶剂以及S-氧化物中硫原子的绝对构型。硫代二糖的结果表明，溶剂极性对糖苷键间构象偏爱的影响很大。在极性溶剂中，旋转异构体的数量P gg和P gt在整个系列中几乎保持恒定，而在非极性溶剂中，观察到gt构象以及糖苷配基对构象平衡的影响。（S S）-和（R S）-烷基硫代硫代生物基S-氧化物系列的结果均显示gt旋转异构体明显占优势，后一序列中的P gt总是比前者高。两个系列均显示糖苷间的P gg和P gt与塔夫脱的空间参数（E S）是指与亚磺酰基相连的烷基，尤其是在非极性溶剂中。周围的C1-S键的立体化学研究确立了解决此联动的灵活性取决于苷元的大小，溶剂的极性，以及硫的绝对构型，所述的衍生物小号小号系列表示在极性和非极性介质更高的灵活性