(5'S)-hydroxymethyl-5'--imidazolidin-2',4'-dione | 781652-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5'S)-hydroxymethyl-5'--imidazolidin-2',4'-dione
• CAS: 781652-99-1
• 化学式: C₉H₁₄N₂O₇
• 分子量: 262.219
• InChiKey: MXSKIFIJOPYSSH-QNDZYWSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.35
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  137.35
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5'S)-hydroxymethyl-5'--imidazolidin-2',4'-dione 在 barium hydroxide octahydrate 作用下， 以 水 为溶剂， 以35%的产率得到methyl (5S)-5-amino-5-C-carboxy-5-deoxy-α-D-lyxo-hexofuranoside
  参考文献：
  名称：

  Synthesis and structure determination of some nonanomerically C–C-linked serine glycoconjugates structurally related to mannojirimycin

  摘要：

  The Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose gave (4'S)-4'-carbamoyl-4'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-oxazolidin-2'-one instead of expected hydantoins. A mixture of hydantoins-(5'R)-triphenylmethoxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione and (5'S)-triphenylmethoxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was obtained from the 5-ulose having protected primary OH group at C-6. The 4'-S configuration of 2 as well as 5'S configuration of (5'S)-hydroxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione (9) was confirmed by X-ray crystallography. Corresponding a-amino acid methyl (5S)-5-amino-5-C-carboxy-5-deoxy-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-beta-L-erythrofuranosid-4-C-yl]-L-serine) (11) was obtained from the hydantoin 9 by acid hydrolysis of the isopropylidene and trityl groups followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5-R configuration, formed in a minority, were also isolated and characterised. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.020
• 作为产物：
  描述：

  (5'S)-triphenylmethoxymethyl-5'--imidazolidin-2',4'-dione 在 溶剂黄146 作用下， 以65%的产率得到(5'S)-hydroxymethyl-5'--imidazolidin-2',4'-dione
  参考文献：
  名称：

  Synthesis and structure determination of some nonanomerically C–C-linked serine glycoconjugates structurally related to mannojirimycin

  摘要：

  The Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose gave (4'S)-4'-carbamoyl-4'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-oxazolidin-2'-one instead of expected hydantoins. A mixture of hydantoins-(5'R)-triphenylmethoxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione and (5'S)-triphenylmethoxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was obtained from the 5-ulose having protected primary OH group at C-6. The 4'-S configuration of 2 as well as 5'S configuration of (5'S)-hydroxymethyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione (9) was confirmed by X-ray crystallography. Corresponding a-amino acid methyl (5S)-5-amino-5-C-carboxy-5-deoxy-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-beta-L-erythrofuranosid-4-C-yl]-L-serine) (11) was obtained from the hydantoin 9 by acid hydrolysis of the isopropylidene and trityl groups followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5-R configuration, formed in a minority, were also isolated and characterised. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.020