(3S,5S)-N-acetyl-3-(N-methylcarbamoyl)-5-(hydroxymethyl)isoxazolidine | 1359096-67-5

• 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: (3S,5S)-N-acetyl-3-(N-methylcarbamoyl)-5-(hydroxymethyl)isoxazolidine
• 英文别名: (3S,5S)-2-acetyl-5-(hydroxymethyl)-N-methyl-1,2-oxazolidine-3-carboxamide
• CAS: 1359096-67-5
• 化学式: C₈H₁₄N₂O₄
• 分子量: 202.21
• InChiKey: ACWBCFAJIDSFOH-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,5S)-acetic acid [2-N-acetyl-3-(N-methylcarbamoyl)isoxazolidin-5-yl]methyl ester 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以98%的产率得到(3S,5S)-N-acetyl-3-(N-methylcarbamoyl)-5-(hydroxymethyl)isoxazolidine
  参考文献：
  名称：

  Cycloaddition of a chiral nitrone to allylic motifs: an access to enantiopure sugar-based amino acids displaying a stable glycosidic bond and to 4(S)-4-hydroxy-l-ornithine

  摘要：

  A (-)-menthone-derived nitrone and various allyl O-, and S-glycosides reacted at 110 degrees C to afford the corresponding cycloadducts in good yields. For an N-acetylated allyl N-glycoside, an N-glycoside-based product was formed in poor yield with loss of the N-acetyl residue, while the major product 4 (60%), in which the sugar moiety was absent, arose from cleavage of the N-glycosidic bond, under the cyclo-addition conditions. The cycloadducts of the O-, and S-glycoside type were ring-opened and subjected to acidic and basic hydrolysis, for removing the chiral auxiliary. This resulted in glycosidic bond cleavage for O-glycosides and loss of material, while an S-glycoside amino acid was isolated in 78% yield, indicating a higher resistance of the S-glycosidic bond. N-O Bond cleavage and hydrolytic treatments applied to 4 afforded 4(S)-4-hydroxy-L-ornithine in high yield. Use of the nitrone derived from (+)-menthone should afford the enantiomer of 4, both precursors of 4-hydroxy arginine derivatives by guanidination. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.048

文献信息

• Cycloaddition of a chiral nitrone to allylic motifs: an access to enantiopure sugar-based amino acids displaying a stable glycosidic bond and to 4(S)-4-hydroxy-l-ornithine
  作者：Kaïss Aouadi、Moncef Msaddek、Jean-Pierre Praly

  DOI：10.1016/j.tet.2011.12.048

  日期：2012.2

  A (-)-menthone-derived nitrone and various allyl O-, and S-glycosides reacted at 110 degrees C to afford the corresponding cycloadducts in good yields. For an N-acetylated allyl N-glycoside, an N-glycoside-based product was formed in poor yield with loss of the N-acetyl residue, while the major product 4 (60%), in which the sugar moiety was absent, arose from cleavage of the N-glycosidic bond, under the cyclo-addition conditions. The cycloadducts of the O-, and S-glycoside type were ring-opened and subjected to acidic and basic hydrolysis, for removing the chiral auxiliary. This resulted in glycosidic bond cleavage for O-glycosides and loss of material, while an S-glycoside amino acid was isolated in 78% yield, indicating a higher resistance of the S-glycosidic bond. N-O Bond cleavage and hydrolytic treatments applied to 4 afforded 4(S)-4-hydroxy-L-ornithine in high yield. Use of the nitrone derived from (+)-menthone should afford the enantiomer of 4, both precursors of 4-hydroxy arginine derivatives by guanidination. (C) 2011 Elsevier Ltd. All rights reserved.