N-[(1S,2S,2'S,3'aS,5R)-2-isopropyl-5,5'-dimethyl-3',3'a-dihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one-2'-yl]-methyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine | 1359096-73-3

• 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: N-[(1S,2S,2'S,3'aS,5R)-2-isopropyl-5,5'-dimethyl-3',3'a-dihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one-2'-yl]-methyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
• CAS: 1359096-73-3
• 化学式: C₃₀H₄₇N₃O₁₁
• 分子量: 625.717
• InChiKey: WWBAAJVVYQBNNT-WWOOQTLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  159.24
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[acetyl(prop-2-enyl)amino]oxan-2-yl]methyl acetate 、 (-)-menthone nitrone 以 甲苯 为溶剂， 反应 72.0h， 以7%的产率得到N-[(1S,2S,2'S,3'aS,5R)-2-isopropyl-5,5'-dimethyl-3',3'a-dihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one-2'-yl]-methyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
  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