N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-propan-2-yloxyoxan-3-yl]acetamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-propan-2-yloxyoxan-3-yl]acetamide
• 化学式: C₁₁H₂₁NO₆
• 分子量: 263.291
• InChiKey: CSHJQINNMOQHDM-APLZJWDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-propan-2-yloxyoxan-3-yl]acetamide 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以92%的产率得到2-氨基-2-脱氧-D-吡喃阿洛糖盐酸盐
  参考文献：
  名称：

  Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

  摘要：

  Palladium-catalyzed oxidation of isopropyl N-acetyl-alpha-D-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.

  DOI：

  10.1021/acs.joc.8b01949
• 作为产物：
  描述：

  isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside 在 sodium tetrahydroborate 、 2,2,2-三氟乙醇 、 [(neocuproine)Pd(μ-OAc)]₂(OTf)₂ 、 对苯醌 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-propan-2-yloxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

  摘要：

  Palladium-catalyzed oxidation of isopropyl N-acetyl-alpha-D-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.

  DOI：

  10.1021/acs.joc.8b01949

文献信息

• Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds
  作者：Ji Zhang、Niek N. H. M. Eisink、Martin D. Witte、Adriaan J. Minnaard

  DOI：10.1021/acs.joc.8b01949

  日期：2019.1.18

  Palladium-catalyzed oxidation of isopropyl N-acetyl-alpha-D-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.