(1S,2S,3S,4S,5S)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octane-2,3,4-triol | 201340-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (1S,2S,3S,4S,5S)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octane-2,3,4-triol
• CAS: 201340-92-3
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: GUPWFRKXADLNQG-REQIZBSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S,5S)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octane-2,3,4-triol 在 molecular sieve 、 溴 、 pyridinium chlorochromate 作用下， 以 吡啶 、 二氯甲烷 、 三氯乙烷 、 水 为溶剂， 生成 Acetic acid (1R,2S,3S,4S,5S)-2,3-diacetoxy-6-acetyl-5-methyl-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]oct-4-yl ester
  参考文献：
  名称：

  Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide

  摘要：

  Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive glycosyl type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-N linked bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydrogenation gave a stable monoalkyl triazene 5 the structure of which was established by X-ray crystallographic analysis. Hydrolysis of 7 allowed access to a monocyclic L-fucose mimic with a nitrogen substituent at C-5. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00378-0
• 作为产物：
  描述：

  (3S,4S,5S,6S)-6-Azidomethyl-2-methyl-tetrahydro-pyran-2,3,4,5-tetraol 在 palladium on activated charcoal 水 、 氢气 作用下， 以85%的产率得到(1S,2S,3S,4S,5S)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octane-2,3,4-triol
  参考文献：
  名称：

  Inhibition of Fucosyl Transferase and Fucosidase by a Rigid Bicyclic Mimic of α-L-Fucose

  摘要：

  A rigid bicyclic analogue of a-L-fucose, prepared from a monoacetonide of L-gulonolactone in an overall yield of 36% without the need for column chromatography, is a potent inhibitor of fucosidases and a weak inhibitor of a fucosyl transferase. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10473-7

文献信息

• Inhibition of Fucosyl Transferase and Fucosidase by a Rigid Bicyclic Mimic of α-L-Fucose
  作者：Annabel R Beacham、Kathryn H Smelt、Keith Biggadike、Christopher J Britten、Lucy Hackett、Bryan G Winchester、Robert J Nash、Rhodri C Griffiths、George W.J Fleet

  DOI：10.1016/s0040-4039(97)10473-7

  日期：1998.1

  A rigid bicyclic analogue of a-L-fucose, prepared from a monoacetonide of L-gulonolactone in an overall yield of 36% without the need for column chromatography, is a potent inhibitor of fucosidases and a weak inhibitor of a fucosyl transferase. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide
  作者：Kathryn H. Smelt、Amanda J. Harrison、Keith Biggadike、Mathias Müller、Keith Prout、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)00378-0

  日期：1999.4

  Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive glycosyl type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-N linked bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydrogenation gave a stable monoalkyl triazene 5 the structure of which was established by X-ray crystallographic analysis. Hydrolysis of 7 allowed access to a monocyclic L-fucose mimic with a nitrogen substituent at C-5. (C) 1999 Elsevier Science Ltd. All rights reserved.