(2R,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | 33600-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS: 33600-54-3
• 化学式: C₁₄H₂₆O₁₀S
• 分子量: 386.42
• InChiKey: QOMRFODAHDHWLQ-XTVRJANMSA-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：

  (2R,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 咪唑 、 重铬酸吡啶 、 四丁基氟化铵 、 乙酸酐 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 Ethyl O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside)uronate
  参考文献：
  名称：

  Westman, Jacob; Nilsson, Marianne, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 949 - 960

  摘要：

  DOI：
• 作为产物：
  描述：

  β-D-麦芽糖八乙酸酯 在 4 Angstroem MS 、 sodium methylate 、 四氯化钛 作用下， 以 甲醇 为溶剂， 反应 6.1h， 生成 (2R,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  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