benzyl 2-acetamido-2-deoxy-α-D-allopyranoside | 86834-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-2-deoxy-α-D-allopyranoside
• 英文别名: N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]acetamide
• CAS: 86834-14-2
• 化学式: C₁₅H₂₁NO₆
• 分子量: 311.335
• InChiKey: SKOZFDIGKDPQBO-ZSAUSMIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  benzyl 2-acetamido-2-deoxy-α-D-allopyranoside 在 palladium 10% on activated carbon 、 水 作用下， 以99%的产率得到N-acetyl-allosamine
  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：

  苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃葡萄糖苷 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 benzyl 2-acetamido-2-deoxy-α-D-allopyranoside
  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

• Synthesis of benzyl 2,3,4-tri-acetamido-2,3,4,6-tetradeoxy-α-d-galactopyranoside
  作者：S.Robert Sarfati、Ladislas Szabó

  DOI：10.1016/0008-6215(83)88099-9

  日期：1983.6
• 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.