[(2S,4S)-2-amino-4-hydroxypentanoic acid-5-yl] 1-thio-β-D-glucopyranoside | 1359096-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,4S)-2-amino-4-hydroxypentanoic acid-5-yl] 1-thio-β-D-glucopyranoside
• 英文别名: (2S,4S)-2-amino-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpentanoic acid
• CAS: 1359096-63-1
• 化学式: C₁₁H₂₁NO₈S
• 分子量: 327.356
• InChiKey: YTYLMUIAUIDFDJ-CBEILUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  199
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-[(3S,5R,6S,9R)-6-isopropyl-1,9-dimethyl-1,4-diazaspiro[4.5]decan-2-one-3-yl]-(2S)-2-hydroxypropyl 1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 盐酸 、 溶剂黄146 、 lithium hydrochloride monohydrate 作用下， 以 水 、 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到[(2S,4S)-2-amino-4-hydroxypentanoic acid-5-yl] 1-thio-β-D-glucopyranoside
  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.