(2S,3R,4S,5R,6R)-2-(((3R,4R,5R,6R)-6-(苄氧基)-4,5-二羟基四氢-2H-吡喃-3-基)氧代)-6-(羟甲基)四氢-2H-吡喃-3,4,5-三醇 | 67412-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S,3R,4S,5R,6R)-2-(((3R,4R,5R,6R)-6-(苄氧基)-4,5-二羟基四氢-2H-吡喃-3-基)氧代)-6-(羟甲基)四氢-2H-吡喃-3,4,5-三醇
• 英文名称: Benzyl-4-O-(β-D-galactopyranosyl)-β-D-xylopyranosid
• 英文别名: (2S,3R,4S,5r,6r)-2-(((3r,4r,5r,6r)-6-(benzyloxy)-4,5-dihydroxytetrahydro-2h-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol；(2S,3R,4S,5R,6R)-2-[(3R,4R,5R,6R)-4,5-dihydroxy-6-phenylmethoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 67412-74-2
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: SKUMUKAMXQEGMM-FNAHJEAMSA-N

物化性质

• 沸点：
  661.7±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苄基-beta-D-木糖苷 、 尾-D-Galactoside,2-nitrophenyl(9CI) 以 水 为溶剂， 以32%的产率得到benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides

  摘要：

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.

  DOI：

  10.1021/jo00083a013

文献信息

• Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides
  作者：Rosa Lopez、Alfonso Fernandez-Mayoralas

  DOI：10.1021/jo00083a013

  日期：1994.2

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
• Controlling yield and regioselectivity in the enzymatic synthesis of β-D-galactopyranosyl-β-D-xylopyranosides
  作者：Rosa López、Alfonso Fernández-Mayoralas

  DOI：10.1016/s0040-4039(00)79118-0

  日期：1992.9

  Yield and regioselectivity of the galactosidation of beta-D-xylopyranosides catalysed by the beta-galactosidase from E. coli can be modulated by the nature of the aglyconic moiety of the xylopyranosides.
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.