phenyl β-D-glucopyranoside sulfoxide | 95593-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl β-D-glucopyranoside sulfoxide
• 英文别名: phenyl β-D-glucopyranosyl sulfoxide；Phenyl-β-D-sulfoxydglucosid；(2S,3R,4S,5S,6R)-2-(benzenesulfinyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 95593-10-5
• 化学式: C₁₂H₁₆O₆S
• 分子量: 288.321
• InChiKey: BMAUZTXADWHSCZ-BRRISTQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl β-D-glucopyranoside sulfoxide 在 β-glucosidase from Trichoderma viride (T.v. A) 、 acetate buffer pH 5 作用下， 生成 D-葡萄糖
  参考文献：
  名称：

  Diastereoselective cleavage of β-glucosylsulfoxides by β-glucosidase

  摘要：

  Phenyl beta-D-glucopyranosyl sulfoxide and p-nitrophenyl beta-D-glucopyranosyl sulfoxide have been diastereoselectively cleaved by beta-glucosidases. Both distereomers can be selectively cleaved, depending on the origin of beta-glucosidase.

  DOI：

  10.1016/s0957-4166(00)86297-7
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 生成 phenyl β-D-glucopyranoside sulfoxide
  参考文献：
  名称：

  Karthaus, Olaf; Shoda, Shin-ichiro; Takano, Hiroshi, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1851 - 1858

  摘要：

  DOI：

文献信息

• Direct aqueous synthesis of non-protected glycosyl sulfoxides; weak inhibitory activity against glycosidases
  作者：Stewart R. Alexander、Andrew J.A. Watson、Antony J. Fairbanks

  DOI：10.1016/j.carres.2015.06.003

  日期：2015.9

  A flavinium catalyst, in conjunction with hydrogen peroxide as stoichiometric oxidant, allowed the aqueous conversion of non-protected thioglycosides into the corresponding glycosyl sulfoxides. These glycosyl sulfoxides displayed only very weak inhibitory activity against corresponding glycosidases. (C) 2015 Elsevier Ltd. All rights reserved.
• Karthaus, Olaf; Shoda, Shin-ichiro; Takano, Hiroshi, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1851 - 1858
  作者：Karthaus, Olaf、Shoda, Shin-ichiro、Takano, Hiroshi、Obata, Kei、Kobayashi, Shiro

  DOI：——

  日期：——
• Diastereoselective cleavage of β-glucosylsulfoxides by β-glucosidase
  作者：Olaf Karthaus、Shin-ichiro Shoda、Shiro Kobayashi

  DOI：10.1016/s0957-4166(00)86297-7

  日期：1994.11

  Phenyl beta-D-glucopyranosyl sulfoxide and p-nitrophenyl beta-D-glucopyranosyl sulfoxide have been diastereoselectively cleaved by beta-glucosidases. Both distereomers can be selectively cleaved, depending on the origin of beta-glucosidase.