p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside | 909795-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyl-5-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 909795-60-4
• 化学式: C₃₄H₄₁NO₆SSi
• 分子量: 619.854
• InChiKey: ISIKOUMIZZLSDO-ZKFZROEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碳酸氢钠 sodium hypochlorite 、 四丁基溴化铵 、 sodium bromide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 1.0h， 以86%的产率得到p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranosyluronic acid
  参考文献：
  名称：

  一种将伯醇氧化成羧酸的简便方法及其在糖胺聚糖合成中的应用。

  摘要：

  开发了一种方便的两步一锅法将伯醇转化为羧酸。首先在相转移条件下用 NaOCl 和 TEMPO 处理醇，然后在一锅中用 NaClO2 氧化。该反应适用于广泛的醇类，温和的反应条件与许多敏感的官能团相容，包括富电子芳环、酸不稳定的异丙叉缩酮和糖苷键，以及易氧化的硫缩醛、对甲氧基苄基和烯丙基部分。通过使用这种新的氧化方案，已经以高产率合成了几种糖胺聚糖，例如肝素、软骨素和透明质酸寡糖。

  DOI：

  10.1002/chem.200600290
• 作为产物：
  描述：

  p-methylphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007

文献信息

• A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids and Its Application in Glycosaminoglycan Syntheses
  作者：Lijun Huang、Nardos Teumelsan、Xuefei Huang

  DOI：10.1002/chem.200600290

  日期：2006.7.5

  two-step, one-pot procedure was developed for the conversion of primary alcohols to carboxylic acids. The alcohol was first treated with NaOCl and TEMPO under phase-transfer conditions, followed by NaClO2 oxidation in one pot. This reaction is applicable to a wide range of alcohols and the mild reaction conditions are compatible with many sensitive functional groups, including electron-rich aromatic rings

  开发了一种方便的两步一锅法将伯醇转化为羧酸。首先在相转移条件下用 NaOCl 和 TEMPO 处理醇，然后在一锅中用 NaClO2 氧化。该反应适用于广泛的醇类，温和的反应条件与许多敏感的官能团相容，包括富电子芳环、酸不稳定的异丙叉缩酮和糖苷键，以及易氧化的硫缩醛、对甲氧基苄基和烯丙基部分。通过使用这种新的氧化方案，已经以高产率合成了几种糖胺聚糖，例如肝素、软骨素和透明质酸寡糖。
• Iterative one-pot syntheses of chitotetroses
  作者：Lijun Huang、Zhen Wang、Xiaoning Li、Xin-shan Ye、Xuefei Huang

  DOI：10.1016/j.carres.2006.01.007

  日期：2006.7

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.