(2S,3S)-N-diphenylmethyl-2-methyl-3-pivaloyloxy-D-4,5-tetrahydropyridine | 243663-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-N-diphenylmethyl-2-methyl-3-pivaloyloxy-D-4,5-tetrahydropyridine
• 英文别名: [(2S,3S)-1-benzhydryl-2-methyl-3,6-dihydro-2H-pyridin-3-yl] 2,2-dimethylpropanoate
• CAS: 243663-12-9
• 化学式: C₂₄H₂₉NO₂
• 分子量: 363.5
• InChiKey: CTLZHXDUNFBVOZ-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-diphenylmethyl-2-methyl-3-pivaloyloxy-D-4,5-tetrahydropyridine 在 palladium on activated charcoal 、 potassium dioxotetrahydroxoosmate(VI) 、 碳酸氢钠 甲基磺酰胺 、 四丁基氢氧化铵 、 氢气 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 3.33h， 生成 (2S,3R,4R,5R)-2-methylpiperidine-3,4,5-triol
  参考文献：
  名称：

  Glycosidase Inhibitors:  Synthesis of Enantiomerically Pure Aza-Sugars from Schiff Base Amino Esters via Tandem Reduction-Alkenylation and Osmylation

  摘要：

  Nitrogen-in-the-ring "aza-sugars" have been synthesized in enantiomerically pure form from the amino acid L-alanine in excellent overall yield. The O'Donnell's Schiff base of L-alanine methyl ester 9a was converted to ate-sugar L-fuco-1-deoxy-nojirimycin, 18, and to the epimer L-gulo-1-deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl- and benzyl-protected (E)-3-lithio-2-propen-1-ols, and the use of these alkenyllithiums with iBu(5)Al(2)H as nucleophiles in the three-selective tandem reduction-alkenylation of the Schiff base esters is described. Osmium-catalyzed cis-oxygenation of the resulting olefin products was selective for the galacto (fuco) amino polyols in all cases for the acyclic olefins, and was gulo-selective for the cyclic D-4,5-dihydropyridine pivalate, 17c. TEMPO-NaOCl was selective for oxidation of the primary position of the acyclic Schiff bases, and allowed for minimal protection/deprotection of the intermediates. The resulting N-benzhydryl heterocycles were easily deprotected with H-2-Pd at atmospheric pressure.

  DOI：

  10.1021/jo9820115
• 作为产物：
  描述：

  (4S,5S,2Z)-5-amino-N-diphenylmethylene-4-pivaloyloxyhex-2-en-1-al 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 (2S,3S)-N-diphenylmethyl-2-methyl-3-pivaloyloxy-D-4,5-tetrahydropyridine
  参考文献：
  名称：

  Glycosidase Inhibitors:  Synthesis of Enantiomerically Pure Aza-Sugars from Schiff Base Amino Esters via Tandem Reduction-Alkenylation and Osmylation

  摘要：

  Nitrogen-in-the-ring "aza-sugars" have been synthesized in enantiomerically pure form from the amino acid L-alanine in excellent overall yield. The O'Donnell's Schiff base of L-alanine methyl ester 9a was converted to ate-sugar L-fuco-1-deoxy-nojirimycin, 18, and to the epimer L-gulo-1-deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl- and benzyl-protected (E)-3-lithio-2-propen-1-ols, and the use of these alkenyllithiums with iBu(5)Al(2)H as nucleophiles in the three-selective tandem reduction-alkenylation of the Schiff base esters is described. Osmium-catalyzed cis-oxygenation of the resulting olefin products was selective for the galacto (fuco) amino polyols in all cases for the acyclic olefins, and was gulo-selective for the cyclic D-4,5-dihydropyridine pivalate, 17c. TEMPO-NaOCl was selective for oxidation of the primary position of the acyclic Schiff bases, and allowed for minimal protection/deprotection of the intermediates. The resulting N-benzhydryl heterocycles were easily deprotected with H-2-Pd at atmospheric pressure.

  DOI：

  10.1021/jo9820115