methyl 3-acetamido-2,3-dideoxy-β-D-arabino-hexopyranoside | 501091-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-2,3-dideoxy-β-D-arabino-hexopyranoside
• 英文别名: Methyl-<3-acetamido-2,3-didesoxy-β-D-arabino-hexopyranosid>；N-[(2R,3S,4R,6R)-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]acetamide
• CAS: 501091-23-2
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: TYYMBFUYLCLHHD-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-azido-2,3-dideoxy-β-D-arabino-hexopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 methyl 3-acetamido-2,3-dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides

  摘要：

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00288-4

文献信息

• The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Marlena Matuszewska、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(02)00288-4

  日期：2002.11

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.