methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldimethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate | 1257516-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldimethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate
• 英文别名: methyl (1R,2S,3S,4R,5R)-3,4-diacetyloxy-5-[tert-butyl(dimethyl)silyl]oxy-1,2-dihydroxycyclohexane-1-carboxylate
• CAS: 1257516-73-6
• 化学式: C₁₈H₃₂O₉Si
• 分子量: 420.532
• InChiKey: OHMGXTQRBBTSKI-FQRJBHLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldimethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Lipase-catalyzed enantio- and regioselective transformation of 3-epi-shikimic acid derivatives as the key step for the entry of polyoxygenated carbacycles

  摘要：

  Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on methyl (+/-)-3,4-di-O-acetyl-5-O-(tert-butyldimethyl)silyl-3-epi-shikimate worked highly regio- and enantioselective manner. Only (3R,4S,5S)-isomer reacted with an E value over 500, exclusively on C-3 acetate. The regio- and enantioselectivity were greatly affected by the substitution pattern on the hydroxy groups. Towards polyoxygenated carbacycles, the above-mentioned highly selective transformation enabled the subsequent stereoselective inversion and dihydroxylation, to give methyl (3S,4R,5S)-3,4,5-triacetoxy-1-cyclohexenecarboxylate [antipode of naturally occurring methyl (-)-3,4,5-tri-O-acetylshikimate], and methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldirnethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.07.009
• 作为产物：
  描述：

  methyl (3S,4R,5R)3,4-diacetoxy-5-(tert-butyldimethyl)silyloxy-1-cyclohexenecarboxylate 在 potassium osmate(VI) dihydrate 、 水 、 N-甲基吗啉氧化物 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以89%的产率得到methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldimethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate
  参考文献：
  名称：

  Lipase-catalyzed enantio- and regioselective transformation of 3-epi-shikimic acid derivatives as the key step for the entry of polyoxygenated carbacycles

  摘要：

  Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on methyl (+/-)-3,4-di-O-acetyl-5-O-(tert-butyldimethyl)silyl-3-epi-shikimate worked highly regio- and enantioselective manner. Only (3R,4S,5S)-isomer reacted with an E value over 500, exclusively on C-3 acetate. The regio- and enantioselectivity were greatly affected by the substitution pattern on the hydroxy groups. Towards polyoxygenated carbacycles, the above-mentioned highly selective transformation enabled the subsequent stereoselective inversion and dihydroxylation, to give methyl (3S,4R,5S)-3,4,5-triacetoxy-1-cyclohexenecarboxylate [antipode of naturally occurring methyl (-)-3,4,5-tri-O-acetylshikimate], and methyl (1R,2S,3S,4R,5R)-3,4-diacetoxy-5-(tert-butyldirnethyl)silyloxy-1,2-dihydroxy-cyclohexanecarboxylate. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.07.009