ethyl 1-thio-gentiobioside | 210223-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-thio-gentiobioside
• CAS: 210223-75-9
• 化学式: C₁₄H₂₆O₁₀S
• 分子量: 386.42
• InChiKey: IRUSSHXXXMBAKA-UHDFQWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.64
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169.3
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-thio-gentiobioside 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 (R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-propionic acid
  参考文献：
  名称：

  痢疾志贺氏菌3型的烯丙糖苷形式与O抗原重复单元相关的封闭五糖衍生物的合成

  摘要：

  从d-半乳糖胺盐酸盐，d-半乳糖和d-葡萄糖开始，四糖衍生物烯丙基2,3,6-三-O-苄基-4-O- [甲基（R）-2-丙酸酯]-β-d-吡喃葡萄糖基-（1→6）-2,3,4-三-O-苄基-α-d-吡喃葡萄糖基-（1→4）-2,6-二-O-苄基-3-O-（3,4已通过嵌段合成策略合成了6-6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃半乳糖苷）-α-d-吡喃半乳糖苷，其中一个嵌段含有甲基（R）-2丙酸酯基。操纵该四糖衍生物的保护基，然后与半乳糖呋喃糖苷供体反应，得到所需的五糖衍生物，其形式为烯丙基糖苷，与痢疾志贺氏菌3型的再生成单元有关。

  DOI：

  10.1081/car-120023471
• 作为产物：
  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

文献信息

• Application of Glycosyl Thioimidates in Solid-Phase Oligosaccharide Synthesis
  作者：M. Cristina Parlato、Medha N. Kamat、Haisheng Wang、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/jo701902f

  日期：2008.3.1

  S-benzoxazolyl (SBox) and S-thiazolinyl (STaz) glycosides, were investigated as glycosyl donors for solid-phase oligosaccharide synthesis. It was demonstrated that these derivatives are suitable for both glycosyl acceptor-bound and glycosyl donor-bound strategies, commonly employed in resin-supported oligosaccharide synthesis.

  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。