methyl 4-azido-4,6-dideoxy-2-O-methanesulfonyl-α-L-idopyranoside | 676127-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-4,6-dideoxy-2-O-methanesulfonyl-α-L-idopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-5-azido-4-hydroxy-2-methoxy-6-methyloxan-3-yl] methanesulfonate
• CAS: 676127-41-6
• 化学式: C₈H₁₅N₃O₆S
• 分子量: 281.29
• InChiKey: BBDNTAQJSWSOHN-BZCSJUTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-4,6-dideoxy-2-O-methanesulfonyl-α-L-idopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到methyl 2,3-anhydro-4-azido-4,6-dideoxy-α-L-gulopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018
• 作为产物：
  描述：

  methyl 3,4-anhydro-6-deoxy-2-O-methanesulfonyl-α-L-altropyranoside 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 作用下， 以63%的产率得到methyl 4-azido-4,6-dideoxy-2-O-methanesulfonyl-α-L-idopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018

文献信息

• 2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products
  作者：Anna Banaszek、Vladimir Zaitsev

  DOI：10.1016/j.tetasy.2003.11.018

  日期：2004.1

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.