6-bromo-6-deoxy-D-galactono-1,4-lactone | 161085-33-2

• 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-galactono-1,4-lactone
• 英文别名: (3R,4R,5R)-5-[(1S)-2-bromo-1-hydroxyethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 161085-33-2
• 化学式: C₆H₉BrO₅
• 分子量: 241.038
• InChiKey: DIFBGJIRMFVVKL-AIHAYLRMSA-N

物化性质

• 熔点：
  126-127 °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-galactono-1,4-lactone 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到6-azido-6-deoxy-D-galactono-1,4-lactone
  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-半乳糖酸-1,4-内酯 在 氢溴酸 作用下， 以40%的产率得到6-bromo-6-deoxy-D-galactono-1,4-lactone
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)89337-6

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.
• Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups
  作者：Omar Cortezano-Arellano、Camilo A. Meléndez-Becerra、Fernando Cortés、Fernando Sartillo-Piscil、Alejandro Cordero-Vargas

  DOI：10.1016/j.carres.2014.04.005

  日期：2014.7

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.
• First synthesis of 4,5-O-isopropylidene-6-thio-d-galactono-1,6-lactone as a precursor of d-galactothioseptanose
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.tetasy.2004.11.088

  日期：2005.2

  Displacement of the bromide group in methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 7, with potassium thioacetate gave methyl 6-(S)-acetyl-2,3 :4,5-di-O-isopropylidene-6-thio-D-galactonate 8 in quantitative yield. Regioselective removal of the 2,3-ketal protecting group afforded methyl 6-(S)-acetyl-4,5-O-isopropylidene-6-thio-D-galactonate 11 in 70% yield. Saponification of compound 11 gave the 6-(S)-4,5-O-isopropylidene-6-thio-D-galactonic acid 12 in quantitative yield. Treatment of 12 with DIC/HOBt as coupling reagents gave, after cyclisation; the target compound: 4,5-O-isopropylidene 6-thio-D-galactono-1,6-lactone 13 in 49% yield. (C) 2005 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.