1,2,3,4-Tetra-O-pivaloyl-β-D-xylopyranose | 100102-41-8

• 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: 1,2,3,4-Tetra-O-pivaloyl-β-D-xylopyranose
• 英文别名: [(3R,4S,5R,6S)-4,5,6-tris(2,2-dimethylpropanoyloxy)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 100102-41-8
• 化学式: C₂₅H₄₂O₉
• 分子量: 486.603
• InChiKey: IYTAVBCDJJGSKN-TWMKSMIVSA-N

物化性质

• 沸点：
  491.3±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetra-O-pivaloyl-β-D-xylopyranose 在 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 4.0h， 以2.87 g的产率得到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
• 作为产物：
  描述：

  D-吡喃木糖 、 三甲基乙酰氯 在 吡啶 作用下， 以91.6%的产率得到1,2,3,4-Tetra-O-pivaloyl-β-D-xylopyranose
  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。
• First cross-coupling reactions on halogenated 1H-1,2,4-triazole nucleosides
  作者：Susanne Wille、Martin Hein、Ralf Miethchen

  DOI：10.1016/j.tet.2006.01.053

  日期：2006.4

  The halogenated 1H-1,2,4-triazole glycosides 6-10 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4-triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), and 3(5)-bromo-5(3)-chloro-1,2,4-triazole (5) with 1,2,3,4-tetra-O-pivaloyl-beta-D-xylopyranose (1). The beta-anomeric major products 3-chloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (6 beta), 3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (7 beta), and 3,5-dibromo-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)1,2,4-triazole (8 beta) were used as starting materials for transition metal catalyzed C-C-coupling reactions. Arylations of the triazole ring of 7 beta, and 8 beta were successful in 5-position with phenylboronic acid, 4-vinylphenylboronic acid, and 4-methoxyphenylboronic acid, respectively, under Suzuki cross-coupling conditions (products 11-17). Moreover, a Cu-catalyzed perfluoroalkylation of 8 beta is reported with 1-iodo-perfluorohexane yielding 3-perfluorohexyl-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (18). Compound 18 was depivaloylated to the trihydroxy derivative 19. The copper-mediated reaction of 8 beta with Rupert's reagent gave the bis(3-bromo-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazol-5-yl) (20). beta 2006 Elsevier Ltd. All rights reserved.
• 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
  作者：Michiko Hori、Fumiaki Nakatsubo

  DOI：10.1016/s0008-6215(01)00100-8

  日期：2001.6

  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.