1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-β-D-ribo-hexopyranose | 501090-96-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-β-D-ribo-hexopyranose
• CAS: 501090-96-6
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: NJVQIBSIYJNLDM-QCNOEVLYSA-N

反应信息

• 作为反应物：
  描述：

  1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-β-D-ribo-hexopyranose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以89%的产率得到3-acetamido-1,6-di-O-acetyl-2,3-dideoxy-β-D-ribo-hexopyranose
  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
• 作为产物：
  描述：

  乙酸酐 、 4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose 在 吡啶 作用下， 反应 0.5h， 生成 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-α-D-arabino-hexopyranose 、 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-β-D-arabino-hexopyranose 、 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-α-D-ribo-hexopyranose 、 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxy-β-D-ribo-hexopyranose
  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