pivaloyl(-3)[pivaloyl(-4)]GalNAc(a)-O-Bn | 592533-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pivaloyl(-3)[pivaloyl(-4)]GalNAc(a)-O-Bn
• 英文别名: [(2R,3R,4R,5R,6S)-5-acetamido-4-(2,2-dimethylpropanoyloxy)-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 592533-31-8
• 化学式: C₂₅H₃₇NO₈
• 分子量: 479.571
• InChiKey: GNLMTRUDBWWVEJ-ADAARDCZSA-N

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：

  pivaloyl(-3)[pivaloyl(-4)]GalNAc(a)-O-Bn 在 palladium on activated charcoal 四氮唑 、 氢气 、 双氧水 、 镍 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 9.0h， 生成 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-acetylamino-5-(2,2-dimethyl-propionyloxy)-6-methoxymethyl-2-phosphonooxy-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 pivaloyl(-3)[pivaloyl(-4)]GalNAc(a)-O-Bn
  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 O-(2-O-sulfo-α-l-idopyranosyluronic acid)-(1 → 3)-2-acetamido-2-deoxy-4-O-sulfo-d-galactopyranose trisodium salt, a disaccharide fragment of dermatan sulfate
  作者：Laurence Rochepeau-Jobron、Jean-Claude Jacquinet

  DOI：10.1016/s0008-6215(97)10017-9

  日期：1997.12

  O -benzyl-2-deoxy- α , and β- d -galactopyranoside, respectively, which served as acceptors in glycosylation reactions with variously activated derivatives of methyl 2-O- benzoyl -3-O- benzyl -4-O- chloroacetyl- l -idopyranuronate . Condensation of the chloride derivative promoted by silver triflate led unexpectedly to the formation of the β-linked disaccharide, whereas the trichloroacetimidoyl derivative

  摘要通过三步操作，将苄基2-乙酰氨基-2-脱氧-α和β-d-吡喃葡萄糖苷高产率地转化为相应的d-半乳糖类似物。这些后来以直接的方式分别转化为苄基2-乙酰氨基-4-O-乙酰基-6-O-苄基-2-脱氧-α和β-d-吡喃半乳糖苷，它们在糖基化反应中以各种方式用作受体。活化的2-O-苯甲酰基-3-O-苄基-4-O-氯乙酰基-1-碘吡喃醛酸酯的衍生物。由三氟甲磺酸银促进的氯化物衍生物的缩合出乎意料地导致了β-连接的二糖的形成，而三氯乙酰亚胺基衍生物以63％的收率提供了预期的α-连接的二糖。随后进行O-脱氯乙酰化，然后在糖醛酸部分的O-4处进行4-甲氧基苄基化，
• 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。