benzyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside | 592533-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside
• 英文别名: pivaloyl(-4)[pivaloyl(-6)]GalNAc(a)-O-Bn；[(2R,3R,4R,5R,6S)-5-acetamido-3-(2,2-dimethylpropanoyloxy)-4-hydroxy-6-phenylmethoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 592533-32-9
• 化学式: C₂₅H₃₇NO₈
• 分子量: 479.571
• InChiKey: PRKBOJPOXLVRNZ-XKRYSZRTSA-N

物化性质

• 沸点：
  622.3±55.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside 在 四氮唑 、 双氧水 、 镍 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-acetylamino-2-(bis-benzyloxy-phosphoryloxy)-6-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases

  摘要：

  A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-alpha-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00287-7
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 benzyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases

  摘要：

  A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-alpha-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00287-7

文献信息

• Synthesis of Novel Di- and Trisaccharide Mimetics with Non-Glycosidic Amino Bridges
  作者：Janna Neumann、Saskia Weingarten、Joachim Thiem

  DOI：10.1002/ejoc.200600958

  日期：2007.3

  Synthesis of novel di- and trisaccharides using enzymatic glycosylation, Dess–Martin oxidation and reductive amination allows rapid access to the target structures. Thus, a novel class of glycomimetics was obtained having nitrogen inserted as bridging atom between two non-anomeric positions. Novel di- and trisaccharide mimetics were designed using N-acetylglucosamine as a basis structure. A third monosaccharide

  使用酶促糖基化、Dess-Martin 氧化和还原胺化合成新型二糖和三糖可以快速获得目标结构。因此，获得了一类新的糖模拟物，其中插入了氮作为两个非异头位置之间的桥接原子。使用 N-乙酰氨基葡萄糖作为基础结构设计了新型二糖和三糖模拟物。第三个单糖单元通过非天然的糖 - 糖键连接，没有异头中心的参与。它们的合成通过氧化、糖基化和还原胺化进行，只需要几个步骤，因此可以快速获得目标结构。通过 Dess-Martin 氧化和随后的还原胺化实现了新型假双糖的生成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,
• Synthesis of UDP-GalNAc analogues as probes for the study of polypeptide-α-GalNAc-transferases. Part 2
  作者：Patricia Busca、Olivier R. Martin

  DOI：10.1016/j.tetlet.2004.04.074

  日期：2004.5

  The synthesis of four UDP-GalNAc analogues (1–4) is described. The 3-, 4- and 6-deoxygenated analogues 1–3 were obtained by way of a divergent strategy starting from a 3,6-di-O-pivaloyl GlcNAc derivative as a common precursor. Analogue 4 bearing a N-trifluoroacetamido group was prepared from the trifluoromethylated oxazoline 24 as key intermediate. These compounds were designed to probe the substrate

  四个UDP-半乳糖胺类似物（合成1 - 4）进行说明。的3-，4-和6-脱氧类似物1 - 3由来自开始发散策略方式获得的3,6-二- ö -pivaloyl的GlcNAc衍生物作为共同的前体。由三氟甲基化的恶唑啉24作为关键中间体制备了带有N-三氟乙酰酰胺基的类似物4。设计这些化合物以探测多肽-α-GalNAc转移酶的底物特异性。