(2R,3R,4S,5S,6R)-2-octoxy-6-(trityloxymethyl)oxane-3,4,5-triol | 724771-78-2

• 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: (2R,3R,4S,5S,6R)-2-octoxy-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 724771-78-2
• 化学式: C₃₃H₄₂O₆
• 分子量: 534.693
• InChiKey: WMFOWTIYYHCKEU-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (2R,3R,4S,5S,6R)-2-octoxy-6-(trityloxymethyl)oxane-3,4,5-triol 在 吡啶 、 咪唑 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 TBDMS(-3)[Trt(-6)]Glc2Ac4Ac(b)-O-octyl
  参考文献：
  名称：

  高效实用的3,6-支链寡糖合成。

  摘要：

  [反应：见正文]描述了3-锅和6-OH差异保护的糖合成子的一锅形成。利用这一新发现制备了甘露吡喃糖基五糖和葡糖吡喃糖基六糖。

  DOI：

  10.1021/ol000243w
• 作为产物：
  描述：

  1-O-辛基-β-D-吡喃葡萄糖苷2,3,4,6-四乙酸盐 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.42h， 生成 (2R,3R,4S,5S,6R)-2-octoxy-6-(trityloxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Chemoenzymatic synthesis of rhodiooctanoside isolated from Chinese medicines, rhodiolae radix

  摘要：

  Direct beta-glucosidation between 1,8-octanediol 5 and D-glucose 6 using the immobilized beta-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave mono-beta-glucoside 3 in 58% yield, which was converted into n-octyl beta-D-glucopyranoside 2 by means of a chemoenzymatic method. The coupling of n-octyl beta-D-glucopyranoside congener 15 and 2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl bromide 17, followed by deprotection afforded the synthetic rhodiooctanoside 1, which was identical with natural 1 with respect to the spectral data and specific rotation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.046

文献信息

• Gastaldi, G.; Focher, B.; Guerrini, M., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 7, p. 1009 - 1024
  作者：Gastaldi, G.、Focher, B.、Guerrini, M.、Alonso, D.

  DOI：——

  日期：——
• Synthesis of sugar-based chelating surfactants for metal removal from wastewater
  作者：Nadège Ferlin、Diego Grassi、Carlos Ojeda、Mariano J.L. Castro、Eric Grand、Alicia Fernández Cirelli、José Kovensky

  DOI：10.1016/j.carres.2008.01.015

  日期：2008.4

  Four chelating surfactants were synthesized in a few steps from octyl D-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important. (C) 2008 Elsevier Ltd. All rights reserved.