1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α- and β-D-glucopyranose | 886997-03-1

• 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: 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α- and β-D-glucopyranose
• 英文别名: 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α/β-D-glucopyranoside；1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α,β-D-glucopyranose；1,3,6-Tri-O-acetyl-2,4-di-O-benzyl-D-glucopyranose；[(2R,3R,4S,5R)-4,6-diacetyloxy-3,5-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 886997-03-1
• 化学式: C₂₆H₃₀O₉
• 分子量: 486.519
• InChiKey: ZAUYNTYUSYJZRN-XGHLBVCRSA-N

物化性质

• 沸点：
  572.0±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α- and β-D-glucopyranose 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 3.5h， 生成 1,6-脱水-2,4-O-苯基-Β-D-吡喃葡萄糖
  参考文献：
  名称：

  Schmidt, Richard R.; Michel, Josef; Ruecker, Ernst, Liebigs Annalen der Chemie, 1989, p. 423 - 428

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 、 乙酸酐 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以35%的产率得到1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α- and β-D-glucopyranose
  参考文献：
  名称：

  烯丙基和苄基4-O-（3,6-二-O-甲基-β-d-吡喃吡喃糖基）-2,3-二-O-甲基-α-1-鼠李糖吡喃糖苷

  摘要：

  摘要2,4-二-O-乙酰基-3,6-二-O-甲基-α-d-吡喃葡萄糖基溴化物与烯丙基或苄基的2,4-二-O-甲基-α-1-鼠李糖吡喃糖苷缩合。氰化汞的存在，然后进行O-脱乙酰基反应，可以极好的收率得到标题寡糖。

  DOI：

  10.1016/0008-6215(87)80099-x

文献信息

• Conformationally Armed 3,6-Tethered Glycosyl Donors: Synthesis, Conformation, Reactivity, and Selectivity
  作者：Mads Heuckendorff、Christian Marcus Pedersen、Mikael Bols

  DOI：10.1021/jo4012464

  日期：2013.7.19

  The reactivity and selectivity of 3,6-tethered glycosyl donors have been studied using acceptors with different steric and electronic characteristics. Eight (four anomeric pairs) 3,6-bridged-glycosyl donors were synthesized in high yields from their common parent sugars. The glycosylation properties were tested using at least three different acceptors and several promoter systems. Thiophenyl 2,4-di-O-benzyl-3,6-O-(di-tert-butylsilylene)-alpha-D-glucopyranoside gave alpha/beta mixtures with standard NIS/TfOH mediated activation, whereas the corresponding fluoride was found to be highly beta-selective, when using SnCl2/AgE(C6F5)(4) as the promoter system. Mannosyl donors were highly alpha-selective despite the altered conformation. Galactosylations using NIS/TfOH were generally alpha-selective, but more beta-selective using the galactosyl fluoride and depending on the acceptor used. Thiophenyl 2-azido-2-deoxy-4-O-benzyl-3,6-O-(di-tert-butylsilylene)-alpha-D-glucopyranoside was found to be alpha-selective. The reactivity of the donors was investigated using competition experiments, and some but not all were found to be highly reactive. Generally it was found that the alpha-thioglycosides were significantly more reactive than the beta; this difference in reactivity was not found for 3,6-anhydro-, armed-(benzylated), or the classic super armed (silylated) donors. A mechanism supporting the unusual observations has been suggested.
• Facile and regioselective preparation of partly O-benzylated d-glucopyranose acetates via acid-mediated simultaneous debenzylation–acetolysis
  作者：Yang Cao、Yasunori Okada、Hidetoshi Yamada

  DOI：10.1016/j.carres.2006.05.018

  日期：2006.9

  Fully O-benzylated methyl alpha-D-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride, Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, and 2-O-benzyl-D-glucopyranose acetates were facilitated in greater than 80% yields. The key points of the preparative reactions were the control of the acid strength and choice of suitable substrates. (c) 2006 Elsevier Ltd. All rights reserved.
• SCHMIDT, RICHARD R.;MICHEL, JOSEF;RUCKER, ERNST, LIEBIGS ANN. CHEM.,(1989) N, C. 423-428
  作者：SCHMIDT, RICHARD R.、MICHEL, JOSEF、RUCKER, ERNST

  DOI：——

  日期：——