1,6-anhydro-2-deoxy-4-O-(p-toluenesulfonyl)-β-D-glucopyranose | 270088-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-deoxy-4-O-(p-toluenesulfonyl)-β-D-glucopyranose
• 英文别名: 1,6-anhydro-2-deoxy-4-O-tosyl-β-D-arabino-hexopyranose；[(1R,2S,3R,5R)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate
• CAS: 270088-60-3
• 化学式: C₁₃H₁₆O₆S
• 分子量: 300.332
• InChiKey: QPXOGLYMSIQQSM-LPWJVIDDSA-N

物化性质

• 沸点：
  509.3±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-deoxy-4-O-(p-toluenesulfonyl)-β-D-glucopyranose 在 吡啶 、 sodium azide 、 sodium methylate 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 29.0h， 生成 1,6-anhydro-4-azido-2,4-dideoxy-β-D-arabino-hexopyranose
  参考文献：
  名称：

  Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra

  摘要：

  通过锂铝氢还原相邻的trans偶氮基对甲苯磺酸酯，制备了一系列1,6-脱水-β-D-己糖苷的2,3,4-三去氧-2,3-表胺和2,3,4-三去氧-3,4-表胺衍生物。观察到从反应基团的trans-二赤道排列的前体中形成环氮丙烷的不寻常现象。讨论了环氮丙烷的NMR和红外光谱。

  DOI：

  10.1135/cccc20041939
• 作为产物：
  描述：

  1,6-脱水-2-脱氧-2-碘-D-吡喃葡萄糖 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 1,6-anhydro-2-deoxy-4-O-(p-toluenesulfonyl)-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and antitumour activity of a new series of nitrosoureido sugars

  摘要：

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00114-8

文献信息

• Synthesis and antitumour activity of a new series of nitrosoureido sugars
  作者：C Monneret

  DOI：10.1016/s0223-5234(00)00114-8

  日期：2000.1

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
  作者：Jindřich Karban、Miloš Buděšínský、Jiří Kroutil

  DOI：10.1135/cccc20041939

  日期：——

  A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

  通过锂铝氢还原相邻的trans偶氮基对甲苯磺酸酯，制备了一系列1,6-脱水-β-D-己糖苷的2,3,4-三去氧-2,3-表胺和2,3,4-三去氧-3,4-表胺衍生物。观察到从反应基团的trans-二赤道排列的前体中形成环氮丙烷的不寻常现象。讨论了环氮丙烷的NMR和红外光谱。