2,3,4-tris-O-(trimethylacetyl)-α-D-xylopyranosyl bromide | 100083-78-1

• 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: 2,3,4-tris-O-(trimethylacetyl)-α-D-xylopyranosyl bromide
• 英文别名: 2,3,4,6-Tetra-O-pivaloyl-α-D-xylopyranosylbromid；2,3,4-tri-O-pivaloyl-α-D-xylopyranosyl bromide
• CAS: 100083-78-1
• 化学式: C₂₀H₃₃BrO₇
• 分子量: 465.382
• InChiKey: HPCQSERJMLJYTH-RQJABVFESA-N

物化性质

• 沸点：
  438.2±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tris-O-(trimethylacetyl)-α-D-xylopyranosyl bromide 在 sodium tetrahydroborate 作用下， 以 乙醚 、 水 为溶剂， 反应 0.25h， 生成 [(3R,4S,5R,6R)-4,5-bis(2,2-dimethylpropanoyloxy)-6-(2H-pyridin-1-yl)oxan-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Stereoselective cycloaddition of N-glycopyranosyl 1,2-dihydropyridines with methyl acrylate.

  摘要：

  DOI：

  10.1016/s0040-4039(00)88898-x
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 2,3,4-tris-O-(trimethylacetyl)-α-D-xylopyranosyl bromide
  参考文献：
  名称：

  Synthesis of d-xylopyranan by the ring-opening polymerization of 3-O-benzyl-α-d-xylopyranose 1,2,4-orthopivalate. Attempts to synthesize a stereoregular polymer

  摘要：

  3-O-Benzpl-alpha -D-xylopyranose 1,2,4-orthopivalate (1) was newly synthesized and polymerized under cationic polymerization reaction conditions in order to synthesize stereoregular (1 --> 4)-beta -D-xylopyranan. Although the polymerization of orthopivalate 1 was carried out under various reaction conditions, a non-stereoregular polymer, but mainly consisting of (1 --> 4)-beta -xylopyranose units, was obtained. Comparing these results with those of glucose 1,2,4-orthopivalates, it was revealed that not only the substituents in the C-2 and C-3 positions, but also the CH2OR group in glucose 1,2,4-orthopivalate, largely contribute to (1 --> 4)-beta -glucosidic bond formation by the ring-opening polymerization. (C) Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00100-8

文献信息

• Stereoselektive Glycosylierung von Steroidalkoholen mit 2,3,4,6-Tetra-O-privaloyl-α-D-glucopyranosylbromid (Pivalobromglucose) und 2,3,4,6-Tetra-O-(o-toluoyl)-α-D-glucopyranosylbromid
  作者：Albrecht Harreus、Horst Kunz

  DOI：10.1002/jlac.198619860411

  日期：1986.4.15

  elektronischen und sterischen Gründen in ihrer Reaktivität differieren und die darüber hinaus empfindliche Gruppierungen enthalten, werden mit 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosylbromid (1) selektiv und effektiv in β-Glucoside übergeführt. Dank des lenkenden Einflusses des 2-O-Pivaloyl-Substituenten wird eine Orthoesterbildung bei den Koenigs-Knorr-Reaktionen stark unterdrückt. Mit dem o-Toluoylrest

  各种结构的甾醇，其羟基官能团由于电子和空间原因而具有不同的反应性，并且还包含敏感基团，它们对2,3,4,6 - tetra - O - pivaloyl -α-D-具有选择性并有效吡喃葡萄糖基溴化物（1）转化为β-葡萄糖苷。由于2- O-新戊酰基取代基的直接影响，在Koenigs-Knorr反应中原酸酯的形成被强烈抑制。用邻甲苯甲酰基作为羟基保护基，这种控制只能在很小的程度上实现。
• Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from <i>Spergularia ramosa</i>
  作者：Ross S. Mancini、Corey A. McClary、Stefi Anthonipillai、Mark S. Taylor

  DOI：10.1021/acs.joc.5b00950

  日期：2015.9.4

  Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.