methyl 2,3-di-O-methyl-4,6-di-O-tosyl-α-D-glucopyranoside | 62847-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-methyl-4,6-di-O-tosyl-α-D-glucopyranoside
• 英文别名: methyl 2,3-di-O-methyl-4,6-di-O-(p-toluenesulfonyl)-α-D-glucopyranoside；Tos(-4)[Tos(-6)]a-Glc1Me2Me3Me；[(2R,3R,4R,5R,6S)-4,5,6-trimethoxy-3-(4-methylphenyl)sulfonyloxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 62847-79-4
• 化学式: C₂₃H₃₀O₁₀S₂
• 分子量: 530.617
• InChiKey: ZMHLWMKZQCIPLE-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-methyl-4,6-di-O-tosyl-α-D-glucopyranoside 在 sodium iodide 作用下， 以 丁酮 为溶剂， 生成 Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A Useful Route to Optically Active 4-Oxygenated 4,5-Dihydroisoxazoles

  摘要：

  Optically active iodotosylates were prepared from carbohydrate precursors and were transformed by the action of excess sodium nitrite/propyl nitrite to bicyclic 4-oxygenated 4,5-dihydro-3-nitroisoxazoles.

  DOI：

  10.1021/jo00103a007
• 作为产物：
  描述：

  methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside 以 吡啶 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 methyl 2,3-di-O-methyl-4,6-di-O-tosyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of monosaccharide-fused azetidines

  摘要：

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00015-3

文献信息

• Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides.
  作者：Zbigniew Pakulski、Donat Pierożyński、Aleksander Zamojski

  DOI：10.1016/s0040-4020(01)87009-5

  日期：1994.2

  Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at −40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading

  在-40℃下，具有被乙酰基或苯甲酰基保护的羟基的糖基硫氰酸氰酸酯易于与格氏试剂反应，以高收率得到相应的烷基或芳基硫代糖苷。在相似条件下形成在其他位置具有SCN基团的单糖衍生物可形成硫醚。轴向硫氰酸盐不反应。升高的温度引起副反应，导致硫醇。
• Synthesis of monosaccharide-fused azetidines
  作者：Thierry Michaud、Josette Chanet-Ray、Sithan Chou、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00015-3

  日期：1997.4

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.
• A Useful Route to Optically Active 4-Oxygenated 4,5-Dihydroisoxazoles
  作者：Peter A. Wade、Sharmila S. Shah、Lakshmi Govindarajan

  DOI：10.1021/jo00103a007

  日期：1994.12

  Optically active iodotosylates were prepared from carbohydrate precursors and were transformed by the action of excess sodium nitrite/propyl nitrite to bicyclic 4-oxygenated 4,5-dihydro-3-nitroisoxazoles.