hepta-O-acetyl-2-hydroxylactal | 14125-80-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: hepta-O-acetyl-2-hydroxylactal
• 英文别名: hepta-O-acetyl-D-lactal；O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol；O²,O³,O⁶-Triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enit；Hepta-O-acetyl-2-hydroxy-D-lactal；[(2R,3R,4S)-4,5-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 14125-80-5
• 化学式: C₂₆H₃₄O₁₇
• 分子量: 618.546
• InChiKey: HKHFGRYHJSJSEU-YWJOQITJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  hepta-O-acetyl-2-hydroxylactal 在 palladium on activated charcoal 三氟化硼乙醚 、 氢溴酸 、 氢气 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 methyl 2,6-di-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of Deoxy Derivatives of Lactose and their Hydrolysis by beta-Galactosidase from E. Coli.

  摘要：

  Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.

  DOI：

  10.3891/acta.chem.scand.46-0186
• 作为产物：
  描述：

  二乙胺 、 2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 氯仿 作用下， 生成 hepta-O-acetyl-2-hydroxylactal
  参考文献：
  名称：

  Maurer, Chemische Berichte, 1930, vol. 63, p. 25,30

  摘要：

  DOI：

文献信息

• Lichtenthaler, Frieder W.; Roenninger, Stephan; Jarglis, Pan, Liebigs Annalen der Chemie, 1989, p. 1153 - 1162
  作者：Lichtenthaler, Frieder W.、Roenninger, Stephan、Jarglis, Pan

  DOI：——

  日期：——
• Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives
  作者：Kun Liu、Shuowei Yao、Yinghan Lou、Yungen Xu

  DOI：10.1016/j.carres.2013.08.022

  日期：2013.11

  In order to find novel potent inhibitors for signal pathways of FGF/FGFR, nineteen N-(3-aryl acryloyl)aminosaccharide derivatives were designed and synthesized based on the binding sites of FGF and oligosaccharides of heparin. Their structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. The nineteen target compounds were evaluated for biological activity against HUVEC cell. In vitro assays showed that compound 10s (IC50 = 5.3 mu M) exhibited comparable inhibitory effects on endothelial cell growth with topotecan (IC50 = 2.7 mu M). Compound 10s (10 mu g/egg) also showed obvious anti-angiogenetic activity in the in vivo chicken chorio allantoic membrane (CAM) assay, and the potency was similar to topotecan (10 mu g/egg). (C) 2013 Elsevier Ltd. All rights reserved.
• LICHTENTHALER, FRIEDER W.;RONNINGER, STEPHAN;JARGLIS, PAN, LIEBIGS ANN. CHEM.,(1989) N2, C. 1153-1161
  作者：LICHTENTHALER, FRIEDER W.、RONNINGER, STEPHAN、JARGLIS, PAN

  DOI：——

  日期：——