ethyl-(O⁴-β-D-glucopyranosyl-1-thio-β-D-glucopyranoside) | 210223-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-(O⁴-β-D-glucopyranosyl-1-thio-β-D-glucopyranoside)
• 英文别名: Aethyl-(O⁴-β-D-glucopyranosyl-1-thio-β-D-glucopyranosid)；Glc(b1-4)Glc(b)-SEt；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-ethylsulfanyl-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 210223-73-7
• 化学式: C₁₄H₂₆O₁₀S
• 分子量: 386.42
• InChiKey: QOMRFODAHDHWLQ-QJGKEIFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl-(O⁴-β-D-glucopyranosyl-1-thio-β-D-glucopyranoside) 在 吡啶 、 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~55.0 ℃ 、3.0 kPa 条件下， 反应 18.5h， 生成 Ethyl 4,6-O-benzylidene-2,3-di-O-benzoyl-β-D-glucopyranosyl-(1→4)-2,3, 6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  与肺炎链球菌3型荚膜多糖片段结构相关的寡糖的合成

  摘要：

  摘要 合成了与肺炎链球菌 3 型荚膜多糖片段结构相关的二糖、三糖和四糖的 3-氨基丙基糖苷。

  DOI：

  10.1007/s11172-017-1708-9
• 作为产物：
  描述：

  ethyl-[O²,O³,O⁶-triacetyl-O⁴-(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 16.0h， 生成 ethyl-(O⁴-β-D-glucopyranosyl-1-thio-β-D-glucopyranoside)
  参考文献：
  名称：

  与肺炎链球菌3型荚膜多糖片段结构相关的寡糖的合成

  摘要：

  摘要 合成了与肺炎链球菌 3 型荚膜多糖片段结构相关的二糖、三糖和四糖的 3-氨基丙基糖苷。

  DOI：

  10.1007/s11172-017-1708-9

文献信息

• Wrede; Hettche, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1927, vol. 172, p. 169,173
  作者：Wrede、Hettche

  DOI：——

  日期：——
• 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
  作者：Suddham Singh、Michaela Scigelova、Peter Critchley、David H.G. Crout

  DOI：10.1016/s0008-6215(97)10030-1

  日期：1997.12

  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.
• Synthesis of oligosaccharides structurally related to fragments of Streptococcus pneumoniae type 3 capsular polysaccharide
  作者：Yu. E. Tsvetkov、D. V. Yashunsky、E. V. Sukhova、E. A. Kurbatova、N. E. Nifantiev

  DOI：10.1007/s11172-017-1708-9

  日期：2017.1

  Abstract3-Aminopropyl glycosides of di-, tri-, and tetrasaccharide structurally related to fragments of Streptococcus pneumoniae type 3 bacteria capsular polysaccharide were synthesized.

  摘要 合成了与肺炎链球菌 3 型荚膜多糖片段结构相关的二糖、三糖和四糖的 3-氨基丙基糖苷。