Trifluoro-methanesulfonic acid (3aS,4R,5R,5aS,8aS,8bS)-5-fluoro-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester | 221682-53-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (3aS,4R,5R,5aS,8aS,8bS)-5-fluoro-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester
• 英文别名: [(1S,2S,6S,7R,8R,9S)-8-fluoro-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl] trifluoromethanesulfonate
• CAS: 221682-53-7
• 化学式: C₁₃H₁₈F₄O₇S
• 分子量: 394.341
• InChiKey: ZAUZVSDGRWKRCR-PXSBVEPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aS,4R,5R,5aS,8aS,8bS)-5-fluoro-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (1S,2S,3R,4R,5S,6R)-6-fluoro-5-azido-1,2,3,4-di-O-isopropylidenecylohexane-1,2,3,4-tetraol
  参考文献：
  名称：

  Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro-allo-inositol

  摘要：

  Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00080-0
• 作为产物：
  描述：

  (1S,2R,3S,4R,5R,6R)-6-fluoro-3,4-O-isopropylidinecylohexane-1,2,3,4,5-pentol 在 对甲苯磺酸 作用下， 以 吡啶 、 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 Trifluoro-methanesulfonic acid (3aS,4R,5R,5aS,8aS,8bS)-5-fluoro-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro-allo-inositol

  摘要：

  Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00080-0