(+)-methyl N-acetyl-4,6-O-diacetyl-α-D-lividosamide | 61348-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-methyl N-acetyl-4,6-O-diacetyl-α-D-lividosamide
• 英文别名: methyl N-acetyl-4,6-di-O-acetyl-α-D-lividosamidine；methyl N-acetyl-4,6-O-diacetyl-α-D-lividosaminide；methyl N-acetyl-α-D-lividosaminide；[(2R,3S,5R,6S)-5-acetamido-3-acetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 61348-65-0
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: LKQVFNGTGDIJNA-XQHKEYJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-2-azido-2,3-dideoxy-5,6-O-isopropylidene-D-ribo-hexofuranose 在 palladium on activated charcoal 氢气 作用下， 以 盐酸 为溶剂， 反应 4.0h， 生成 (+)-methyl N-acetyl-4,6-O-diacetyl-α-D-lividosamide
  参考文献：
  名称：

  The electron-releasing homoconjugated carbonyl group. Application to the total syntheses of 3-deoxy-, 4-deoxy-hexose, lividosamine and derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)70712-x

文献信息

• Synthesis of 2-Nitroglycals from Glycals Using the Tetrabutylammonium Nitrate–Trifluoroacetic Anhydride–Triethylamine Reagent System and Base-Catalyzed Ferrier Rearrangement of Acetylated 2-Nitroglycals
  作者：Suresh Dharuman、Preeti Gupta、Pavan K. Kancharla、Yashwant D. Vankar

  DOI：10.1021/jo401165y

  日期：2013.9.6

  A reagent system comprising tetrabutylammonium nitrate–trifluoroacetic anhydride–triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products

  已开发出一种由硝酸四丁铵-三氟乙酸酐-三乙胺组成的试剂系统，用于从各种受保护的糖类合成2-硝基糖类。首次报道了在三-O-乙酰化的2-硝基糖上的碱催化的Feer重排。已经检查了这些硝基乙酸盐的反应性和相关的选择性，并且将某些产物转化为2，3-二氨基-2，3-二脱氧糖苷和甲基N-乙酰基-d- lividosaminide。
• Conversion of Glycals to 1-Azido-2-iodo Sugars Using <i>N</i>-Iodosuccinimide/Sodium­ Azide or Potassium Iodide/Oxone Reagent Systems: Application in the Synthesis of Methyl <i>N</i>-Acetyl-α-<scp>d</scp>-lividosaminide
  作者：Yashwant Vankar、Girish Rawal、Shikha Rani、K. Madhusudanan

  DOI：10.1055/s-2006-958943

  日期：2007.1

  Glycals are readily converted into the corresponding 2-deoxy-2-iodoglycosyl azides, in good to excellent yields in a short time, upon treatment with N-iodosuccinimide/sodium azide or potassium iodide/Oxone reagent systems. One of these 1-azido-2-iodo sugars was converted into methyl N-acetyl-a-d-lividosaminide.

  在用 N-碘代琥珀酰亚胺/叠氮化钠或碘化钾/Oxone 试剂系统处理后，糖醇很容易转化为相应的 2-脱氧-2-碘糖基叠氮化物，并在短时间内以良好至极好的收率。这些 1-azido-2-iodo 糖中的一种被转化为甲基 N-乙酰-ad-lividosaminide。
• A convenient synthesis of methyl N-acetyl-α-d-lividosaminide from d-glucal
  作者：B.Gopal Reddy、Yashwant D Vankar

  DOI：10.1016/s0040-4039(03)01044-x

  日期：2003.6

  Methyl N-acetyl-alpha-D-lividosaminide has been synthesised starting from 4,6-di-O-benzyl-D-glucal via a new nitro glucal derivative in six steps. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Total asymmetric syntheses of d-lividosamine and 2-acetamido-2,3-dideoxy-d-arabino-hexose derivatives.
  作者：Etienne de Buchteneere、Daniela Fattori、Pierre Vogel

  DOI：10.1016/s0040-4020(01)88357-5

  日期：1992.11
• FATTORI, DANIELA;GUCHTENEERE, ETIENNE DE;VOGEL, PIERRE, TETRAHEDRON LETT., 30,(1989) N2, C. 7415-7418
  作者：FATTORI, DANIELA、GUCHTENEERE, ETIENNE DE、VOGEL, PIERRE

  DOI：——

  日期：——