(S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-amino]-4-methyl-pentanoic acid methyl ester | 336110-48-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-amino]-4-methyl-pentanoic acid methyl ester
• 英文别名: methyl (2S)-2-[[(3aR,6R,6aR)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]methylamino]-4-methylpentanoate
• CAS: 336110-48-6
• 化学式: C₁₅H₂₅NO₆
• 分子量: 315.367
• InChiKey: KUTAUFNFPZISAK-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-amino]-4-methyl-pentanoic acid methyl ester 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以96%的产率得到(S)-2-((3aR,7R,7aR)-7-Hydroxy-2,2-dimethyl-4-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl)-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams

  摘要：

  A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of D-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel(R) resin, and the lactamisation step was concomitant with the cleavage from the resin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02146-8
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 potassium carbonate 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-amino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams

  摘要：

  A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of D-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel(R) resin, and the lactamisation step was concomitant with the cleavage from the resin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02146-8

文献信息

• Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams
  作者：Jordi Piró、Mario Rubiralta、Ernest Giralt、Anna Diez

  DOI：10.1016/s0040-4039(00)02146-8

  日期：2001.1

  A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of D-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel(R) resin, and the lactamisation step was concomitant with the cleavage from the resin. (C) 2001 Elsevier Science Ltd. All rights reserved.