(1S,2S,3R,4S,5R)-4-Amino-1-hydroxymethyl-cyclohexane-1,2,3,5-tetraol | 183505-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4S,5R)-4-Amino-1-hydroxymethyl-cyclohexane-1,2,3,5-tetraol
• 英文别名: (1S,2S,3R,4S,5R)-4-amino-1-(hydroxymethyl)cyclohexane-1,2,3,5-tetrol
• CAS: 183505-11-5
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: LHPZDTPUUCHBOS-UOYQFSTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1S,2S,3R,4S,5R)-4-Amino-1-hydroxymethyl-cyclohexane-1,2,3,5-tetraol 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以75%的产率得到Acetic acid (1S,2S,4R,5S,6R)-4,6-diacetoxy-2-acetoxymethyl-5-acetylamino-2-hydroxy-cyclohexyl ester
  参考文献：
  名称：

  Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

  摘要：

  Valiolamine (1), 1-epi-valiolamine (2), 2-epi-valiolamine (3), (1R,2R)-valiolamine (4), and 2-amino regioisomer 17 have been prepared from (-)-quinic acid (6) in 14 (8.4% overall yield), 13 (9.0%), 15 (4.3%), 17 steps (2.5%), and 12 steps (13%), respectively. Charged nucleophilic ring-openings of cyclic sulfate (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4,5-pentol (11) occurred regioselectively at C-2, whereas the corresponding ring-openings of its (1S,2R)-diastereomer 34 proceeded preponderantly at C-1. (1R,2S,3R,4S,5S)-2,4,5-Tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl) cyclohexane-1,2,3,4,5-pentol (24) underwent novel internal displacement spontaneously to form (1S,2S,3R,4S,5S)-1,2,4-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,2,3,4,5-pentol (25), whereas its 2-epimer was inert under the same conditions. Ruthenium-catalyzed dihydroxylation of alkene, (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol (31), gave the desired beta-1,2-diol 32 in higher yield and stereoselectivity than the osmium tetraoxide protocol. The regioselectivity of charged nucleophilic ring-openings of cyclic sulfates 11, 34, and 38 is discussed.

  DOI：

  10.1021/jo9607828
• 作为产物：
  描述：

  (1R,2S,3R,4S,5S)-2-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,3,4,5-tetrol 在 palladium hydroxide - carbon 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.5h， 生成 (1S,2S,3R,4S,5R)-4-Amino-1-hydroxymethyl-cyclohexane-1,2,3,5-tetraol
  参考文献：
  名称：

  Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

  摘要：

  Valiolamine (1), 1-epi-valiolamine (2), 2-epi-valiolamine (3), (1R,2R)-valiolamine (4), and 2-amino regioisomer 17 have been prepared from (-)-quinic acid (6) in 14 (8.4% overall yield), 13 (9.0%), 15 (4.3%), 17 steps (2.5%), and 12 steps (13%), respectively. Charged nucleophilic ring-openings of cyclic sulfate (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4,5-pentol (11) occurred regioselectively at C-2, whereas the corresponding ring-openings of its (1S,2R)-diastereomer 34 proceeded preponderantly at C-1. (1R,2S,3R,4S,5S)-2,4,5-Tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl) cyclohexane-1,2,3,4,5-pentol (24) underwent novel internal displacement spontaneously to form (1S,2S,3R,4S,5S)-1,2,4-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,2,3,4,5-pentol (25), whereas its 2-epimer was inert under the same conditions. Ruthenium-catalyzed dihydroxylation of alkene, (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol (31), gave the desired beta-1,2-diol 32 in higher yield and stereoselectivity than the osmium tetraoxide protocol. The regioselectivity of charged nucleophilic ring-openings of cyclic sulfates 11, 34, and 38 is discussed.

  DOI：

  10.1021/jo9607828