2-Acetamido-2-deoxy-3,4,6-tri-O-benzoyl-α-D-glucopyranose | 101904-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetamido-2-deoxy-3,4,6-tri-O-benzoyl-α-D-glucopyranose
• 英文别名: 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranose；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-dibenzoyloxy-6-hydroxyoxan-2-yl]methyl benzoate
• CAS: 101904-02-3
• 化学式: C₂₉H₂₇NO₉
• 分子量: 533.535
• InChiKey: KESYOCSVVBUWEQ-LPSUVQJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  137.46
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-Acetamido-2-deoxy-3,4,6-tri-O-benzoyl-α-D-glucopyranose 生成 [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyphosphinic acid;N,N-diethylethanamine
  参考文献：
  名称：

  NIKOLAEV, A. V.;IVANOVA, I. A.;SHIBAEV, V. N., BIOORGAN. XIMIYA, 16,(1990) N2, S. 1693-1695

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Acetamido-2-deoxy-1,3,4,6-tetra-O-benzoyl-D-glucopyranose 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到2-Acetamido-2-deoxy-3,4,6-tri-O-benzoyl-α-D-glucopyranose
  参考文献：
  名称：

  A Facile Regioselective 1-O-Deacylation of Peracylated Glycopyranoses

  摘要：

  描述了在极性非质子溶剂中，使用氨对过酰化的糖吡喃醇1-5进行区域选择性去酰基化，得到相应的α-1-OH糖衍生物6-10，总体或高立体选择性。

  DOI：

  10.1055/s-1985-31446

文献信息

• WO2007/93769
  申请人：——

  公开号：——

  公开（公告）日：——
• An efficient conversion of N-acetyl-d-glucosamine to N-acetyl-d-galactosamine and derivatives
  作者：Jianhao Feng、Chang-Chun Ling

  DOI：10.1016/j.carres.2010.09.008

  日期：2010.11

  2-Acetamido-2-deoxy-D-galactose (D-GalNAc) is an important monosaccharide widely distributed in nature. However, unlike its 4-epimer, the 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-GalNAc is very expensive to obtain from commercial sources. Herein we report an efficient transformation that allows for the conversion of D-GlcNAc to a D-GalNAc derivative 7 in three steps and in 58.4-75% overall yields. The process was carried out on a greater than 20-g scale without the need of chromatography. The versatility of compound 7 was demonstrated by the synthesis of several useful monosaccharides and thiodisaccharides containing a D-GalNAc residue. (C) 2010 Elsevier Ltd. All rights reserved.
• Hexose-modified anti-viral analogues of uridine 5′-disphosphate glucose derivatives
  作者：José Fiandor、María-Teresa Garcìa-López、Federico G De Las Heras、Paloma P Méndez-Castrillón、Ana San Félix、Balbino Alarcón、Luis Carrasco

  DOI：10.1016/0223-5234(87)90174-7

  日期：1987.1