3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose | 68095-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose
• 英文别名: O³,O⁵-diacetyl-O¹,O²-isopropylidene-O⁶-trityl-α-D-glucofuranose；O³,O⁵-Diacetyl-O¹,O²-isopropyliden-O⁶-trityl-α-D-glucofuranose；[(3aR,5R,6S,6aR)-5-[(1R)-1-acetyloxy-2-trityloxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 68095-73-8
• 化学式: C₃₂H₃₄O₈
• 分子量: 546.617
• InChiKey: WGCVJNPEVHKYOG-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose 在 溶剂黄146 作用下， 生成 3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Virtual 1H-1H spin-spin coupling in a linear five-spin system on the pyranose rings of some glucuronides

  摘要：

  In the H-1 NMR spectra of methyl 2,3,4-tri-O-acetyl-beta D-glucopyranosyluronate-(1 --> 3)- 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (6) and methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyluronate-(l --> 6)-1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose (7), which were obtained by the reaction of 1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose (1) with methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide (5) in the presence of Hg(CN), in 1:1 benzene-nitromethane at 45 degrees C, protons on both beta-D-glucopyranosyluronate rings were observed as very complex signals that could not be interpreted by first-order analysis. Similar complex signals were also observed for the protons on the beta-D-glucopyranosyluronate rings that were sugar components of some triterpenoidal glycosides (13-15). These complex signals were determined to be due to virtual long-range spin-spin coupling in the linear five-spin system on the glucopyranosyluronate rings of the glucuronides by H-1, C-13, H-C COSY, 1D HOHAHA, and spin-simulation spectroscopies.

  DOI：

  10.1016/0008-6215(94)84075-x
• 作为产物：
  描述：

  双丙酮葡萄糖 在 吡啶 、 Amberlite IR-120 (H⁺ form) 作用下， 以 甲醇 、 水 为溶剂， 反应 62.0h， 生成 3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose
  参考文献：
  名称：

  Virtual 1H-1H spin-spin coupling in a linear five-spin system on the pyranose rings of some glucuronides

  摘要：

  In the H-1 NMR spectra of methyl 2,3,4-tri-O-acetyl-beta D-glucopyranosyluronate-(1 --> 3)- 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (6) and methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyluronate-(l --> 6)-1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose (7), which were obtained by the reaction of 1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose (1) with methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide (5) in the presence of Hg(CN), in 1:1 benzene-nitromethane at 45 degrees C, protons on both beta-D-glucopyranosyluronate rings were observed as very complex signals that could not be interpreted by first-order analysis. Similar complex signals were also observed for the protons on the beta-D-glucopyranosyluronate rings that were sugar components of some triterpenoidal glycosides (13-15). These complex signals were determined to be due to virtual long-range spin-spin coupling in the linear five-spin system on the glucopyranosyluronate rings of the glucuronides by H-1, C-13, H-C COSY, 1D HOHAHA, and spin-simulation spectroscopies.

  DOI：

  10.1016/0008-6215(94)84075-x

文献信息

• Josephson, Justus Liebigs Annalen der Chemie, 1929, vol. 472, p. 217,228
  作者：Josephson

  DOI：——

  日期：——
• Klemer, Almuth; Bieber, Michael; Wilbers, Hubert, Liebigs Annalen der Chemie, 1983, # 8, p. 1416 - 1421
  作者：Klemer, Almuth、Bieber, Michael、Wilbers, Hubert

  DOI：——

  日期：——