methyl 2-acetamido-2-deoxy-β-D-glucofuranoside | 5517-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-β-D-glucofuranoside
• 英文别名: methyl-(2-acetylamino-2-deoxy-β-D-glucofuranoside)；Methyl-(2-acetylamino-2-desoxy-β-D-glucofuranosid)；N-[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-methoxyoxolan-3-yl]acetamide
• CAS: 5517-54-4
• 化学式: C₉H₁₇NO₆
• 分子量: 235.237
• InChiKey: ITYWONYUGBJWSH-JGKVKWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-β-D-glucofuranoside 在 乙酸铵 、 溴 、 三正丁基甲氧基锡 、 二正丁基氧化锡 、 sodium cyanoborohydride 作用下， 以 甲醇 、 硫酸 为溶剂， 反应 3.25h， 生成 2-乙酰氨基-1,2,5-三脱氧-1,5-亚氨基-d-葡萄糖醇
  参考文献：
  名称：

  2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis

  摘要：

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

  DOI：

  10.1016/s0040-4020(01)80229-5
• 作为产物：
  描述：

  2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 在 对甲苯磺酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 methyl 2-acetamido-2-deoxy-β-D-glucofuranoside
  参考文献：
  名称：

  2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis

  摘要：

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

  DOI：

  10.1016/s0040-4020(01)80229-5

文献信息

• The hydration heat of the benzenesulphonate ion
  作者：D.F.C. Morris

  DOI：10.1016/0040-4020(58)80064-2

  日期：1958.1
• Chemistry of the neomycins. XIII. Synthesis of aminocyclitols and aminosugars via nitromethane condensations
  作者：Seiichiro Ogawa、Kenneth L. Rinehart、Goro Kimura、Robert P. Johnson

  DOI：10.1021/jo00920a015

  日期：1974.3
• Facile Approach to 2-Acetamido-2-deoxy-β-<scp>d</scp>-Glucopyranosides via a Furanosyl Oxazoline
  作者：Ye Cai、Chang-Chun Ling、David R. Bundle

  DOI：10.1021/ol051523k

  日期：2005.9.1

  A concise and convenient route that may be easily scaled is reported for the preparation of unprotected beta-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding beta-D-glucopyranosides in good to high yields. Primary alcohols gave only beta-D-glucopyranosides. A mechanism is proposed for this transformation.
• 2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis
  作者：Richard H. Furneaux、Graeme J. Gainsford、Gregory P. Lynch、Selwyn C. Yorke

  DOI：10.1016/s0040-4020(01)80229-5

  日期：——

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.