1,2-O-isopropylidene-β-D-tagatopyranose | 124338-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-β-D-tagatopyranose
• 英文别名: (5S,6S,7S,8R)-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decane-6,7,8-triol
• CAS: 124338-71-2
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: NCPKAWHTYZABFG-XKBZYTNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-β-D-tagatopyranose 、 4-硝基苯基-D-吡喃葡糖苷 在 β-D-galactosidase from Aspergillus oryzae 作用下， 以 phosphate buffer 为溶剂， 以7.7%的产率得到5-O-(β-D-galactopyranosyl)-1,2-O-isopropylidene-β-D-tagatopyranose
  参考文献：
  名称：

  ENZYMATIC O-GALACTOSYLATION OF SELECTED FREE AS WELL AS PARTIALLY PROTECTED KETOHEXOSES

  摘要：

  A range of partially protected ketoses was O-galactosylated with P-galactosidase from Aspergillus oryzae employing (4-nitro)phenyl beta -D-galactopyranoside as the donor. This enzyme also accepted free D-tagatose as a substrate.

  DOI：

  10.1081/car-100108279
• 作为产物：
  描述：

  3,4,5-tri-O-acetyl-1,2-O-isopropylidene-β-D-tagatopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以200 mg的产率得到1,2-O-isopropylidene-β-D-tagatopyranose
  参考文献：
  名称：

  3,4-Anhydro-1,2-O-isopropylidene-β-d-tagatopyranose and 4,5-anhydro-1,2-O-isopropylidene-β-d-fructopyranose

  摘要：

  3,4-Anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose (8) and 4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O- isopropylidene-4-O-toluene-p-sulfonyl-beta-D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl-1,2-O-isopropylidene-beta-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene-beta-D-tagatopyranose, respectively.

  DOI：

  10.1016/s0008-6215(99)00272-4

文献信息

• 3,4-Anhydro-1,2-O-isopropylidene-β-d-tagatopyranose and 4,5-anhydro-1,2-O-isopropylidene-β-d-fructopyranose
  作者：Masoud Ataie、J.Grant Buchanan、Alan R Edgar、Richard G Kinsman、Maria Lyssikatou、Mary F Mahon、Pauline M Welsh

  DOI：10.1016/s0008-6215(99)00272-4

  日期：1999.1

  3,4-Anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose (8) and 4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O- isopropylidene-4-O-toluene-p-sulfonyl-beta-D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl-1,2-O-isopropylidene-beta-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene-beta-D-tagatopyranose, respectively.
• IZQUIERDO, CUBERO I.;LOPEZ-ESPINOSA, M. T. PLAZA, ANAL. QUIM., 86,(1990) N, C. 554-560
  作者：IZQUIERDO, CUBERO I.、LOPEZ-ESPINOSA, M. T. PLAZA

  DOI：——

  日期：——
• ENZYMATIC O-GALACTOSYLATION OF SELECTED FREE AS WELL AS PARTIALLY PROTECTED KETOHEXOSES
  作者：Brigitte Eder、Inge Lundt、Arnold Stütz、Tanja Wrodnigg

  DOI：10.1081/car-100108279

  日期：——

  A range of partially protected ketoses was O-galactosylated with P-galactosidase from Aspergillus oryzae employing (4-nitro)phenyl beta -D-galactopyranoside as the donor. This enzyme also accepted free D-tagatose as a substrate.