2-Phenylethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 10548-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Phenylethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: 2-Phenylaethyl-tri-O-acetyl-β-D-xylopyranosid；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-(2-phenylethoxy)oxan-3-yl] acetate
• CAS: 10548-54-6
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: XBARERUDUZTPAK-FCGDIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Phenylethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以90%的产率得到2-phenylethyl 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
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基吡喃戊糖 在 calcium sulfate 、 氢溴酸 、 calcium carbonate 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 2-Phenylethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis and conformational analysis of the plant hormone (auxin) related 2-(indol-3-yl)ethyl and 2-phenylethyl β-d-xylopyranosides and their 2,3,4-tri-O-acetyl derivatives

  摘要：

  The synthesis, structure analysis by X-ray diffraction and NMR spectroscopy (including also H-1 {H-1}NOE measurements), as well as molecular mechanics and dynamics of D-xylopyranose conjugates of 2-(indol-3-yl)ethanol (1) and 2-phenylethanol (2) are described. The per-O-acetylated derivatives of 2-(indol-3-yl)ethyl beta-D-xylopyranoside (4 beta) and 2-phenylethyl beta-D-xylopyranoside (7 beta) were prepared [along with corresponding alpha-D-isomers (4 alpha and 7 alpha) and 1,2-O-orthoacetates (5,8)] by Koenigs-Knorr condensation of the aglycone alcohols with 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl bromide. Glycoside 4 beta was deprotected to yield 2-(indol-3-yl) ethyl beta-D-xylopyranoside (6). The crystal structures of 4 beta and 7 beta were determined. The crystals of both compounds are monoclinic, space group P 2(1) with a = 11.985(1), b = 7.317(1), c = 12.428(1) Angstrom, beta = 93.2(1)degrees, Z = 2 (4 beta); a = 5.809(1), b = 19.833(1), c = 8.912(1) Angstrom, beta = 106.0(1)degrees, Z = 2 (7 beta). The beta-D-xylopyranose rings are in the C-4(1) chair conformation. The results of the theoretical conformational analysis are compared with the values obtained from the experimental measurements in solid state and solution.

  DOI：

  10.1016/0008-6215(95)00037-t