(R)-2-tert-Butoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine | 219927-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-tert-Butoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine
• 英文别名: (1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxy]ethanamine
• CAS: 219927-56-7
• 化学式: C₁₁H₂₃NO₃
• 分子量: 217.309
• InChiKey: FDNHDHMAOHOMCZ-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 (R)-2-tert-Butoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine 以 苯 为溶剂， 反应 48.0h， 以54%的产率得到1,4-bis-tert-butoxy-3(R)-amino-2(S)-butanol
  参考文献：
  名称：

  Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group

  摘要：

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.

  DOI：

  10.1021/jo981579a
• 作为产物：
  描述：

  1.2;3.4-Di-O-isopropyliden-D-threit 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 176.0h， 生成 (R)-2-tert-Butoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine
  参考文献：
  名称：

  Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group

  摘要：

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.

  DOI：

  10.1021/jo981579a

文献信息

• Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group
  作者：Wen-Lung Cheng、Yeng-Jeng Shaw、Sue-Min Yeh、Puthuparampil P. Kanakamma、Yu-Huey Chen、Chuo Chen、Jia-Cheng Shieu、Shaang-Jyh Yiin、Gene-Hsiang Lee、Yu Wang、Tien-Yau Luh

  DOI：10.1021/jo981579a

  日期：1999.1.1

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.