methyl 3-acetamido-4,6-di-O-acetyl-2,3-dideoxy-α-D-lyxo-hexopyranoside | 3369-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-4,6-di-O-acetyl-2,3-dideoxy-α-D-lyxo-hexopyranoside
• 英文别名: Methyl-3-acetamino-4.6-di-O-acetyl-2.3-dideoxy-α-D-lyxo-hexopyranosid；[(2R,3R,4R,6S)-4-acetamido-3-acetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 3369-63-9；4677-56-9；16697-57-7
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: SXDFOACOYIIQPT-FVCCEPFGSA-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：

  乙酸酐 、 在 palladium on activated charcoal 氢气 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以31%的产率得到methyl 3-acetamido-4,6-di-O-acetyl-2,3-dideoxy-α-D-xylo-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