(2S,3R,4S,5R)-2-benzyl-3,4,5-tris(phenylmethoxy)oxan-2-ol | 153751-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4S,5R)-2-benzyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• CAS: 153751-47-4
• 化学式: C₃₃H₃₄O₅
• 分子量: 510.63
• InChiKey: NVDAUTBMHNKWSJ-LVVLYVGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-benzyl-3,4,5-tris(phenylmethoxy)oxan-2-ol 在 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (2S,3S,4S,5R)-2-benzyl-3,4,5-tris(phenylmethoxy)oxane
  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
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-xylopyranose 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.75h， 生成 (2S,3R,4S,5R)-2-benzyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
  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%.