6-bromo-6-deoxy-D-mannono-1,4-lactone | 161085-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-bromo-6-deoxy-D-mannono-1,4-lactone
• 英文别名: (3S,4R,5S)-5-[(1S)-2-bromo-1-hydroxyethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 161085-43-4
• 化学式: C₆H₉BrO₅
• 分子量: 241.038
• InChiKey: DIFBGJIRMFVVKL-SQOUGZDYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  429.2±18.0 °C(Predicted)
• 密度：
  2.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-6-deoxy-D-mannono-1,4-lactone 在 palladium on activated charcoal sodium tetrahydroborate 、 叠氮化锂 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-氨基-1-脱氧-D-甘露糖醇
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以69%的产率得到6-bromo-6-deoxy-D-mannono-1,4-lactone
  参考文献：
  名称：

  Improved synthesis of 6-amino-6-deoxy-d-galactono-1,6-lactam and d-mannono-1,6-lactam from corresponding unprotected d-hexono-1,4-lactones

  摘要：

  Regioselective bromination of unprotected D-galactono-1,4-lactone and D-mannono-1,4-lactone with PPh3/CBr4 led to 6-bromo-6-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 6-amino-6-deoxy-D-galactono-1,6-lactam (8) and 6-amino-6-deoxy-D-mannono-1,6-lactam (13) in 74 and 67% overall yield, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.062

文献信息

• Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors
  作者：Inge Lundt、Holger Frank

  DOI：10.1016/s0040-4020(01)89337-6

  日期：1994.1

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.
• Direct syntheses of S-alkylthio-d-galactono-, d-mannono-1,4-lactones, S-alkylthio-l-galactitols and d-mannitols displaying amphiphilic and mesophasic properties
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.carres.2004.05.004

  日期：2004.7

  Alkylthi-L-galactitols and D-mannitols were obtained in good yields (70-81%) by reduction, with NaBH4, of the corresponding 6-S-alkyl-6-thio-D-hexono-1,4-lactones. (C) 2004 Elsevier Ltd. All rights reserved.
• Improved synthesis of 6-amino-6-deoxy-d-galactono-1,6-lactam and d-mannono-1,6-lactam from corresponding unprotected d-hexono-1,4-lactones
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.tet.2003.12.062

  日期：2004.2

  Regioselective bromination of unprotected D-galactono-1,4-lactone and D-mannono-1,4-lactone with PPh3/CBr4 led to 6-bromo-6-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 6-amino-6-deoxy-D-galactono-1,6-lactam (8) and 6-amino-6-deoxy-D-mannono-1,6-lactam (13) in 74 and 67% overall yield, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
• The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.tetasy.2006.04.018

  日期：2006.5

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.