tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate | 799267-32-6

• 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: tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate
• 英文别名: tert-butyl (2S,5S)-6-azido-5-hydroxy-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 799267-32-6
• 化学式: C₁₈H₂₆N₄O₅
• 分子量: 378.428
• InChiKey: FZKYHPRMWPLVBB-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate 在 叔丁基二甲硅基三氟甲磺酸酯 、 zinc diacetate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 生成 tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate
  参考文献：
  名称：

  Hydroxylysine containing glycoconjugates: an efficient synthesis of natural galactosylhydroxylysine (Gal-Hyl) and glucosylgalactosylhydroxylysine (Glu-Gal-Hyl) and of their (5S)-epimers

  摘要：

  The paper reports the first chemical synthesis of alpha-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-5-O-hydroxylysine, a biological marker of bone resorption and of its unnatural (5S)-epimer, starting from commercial sugars and amino acids. Moreover, the synthetic protocol set-up has resulted in a new procedure for the synthesis of the beta-D-galactopyranosyl-5-O-hydroxylysine and its unnatural (5S)-epimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.006
• 作为产物：
  描述：

  O-tert-butyl-N,N'-dicyclohexylisourea 、 (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 以 二氯甲烷 为溶剂， 反应 120.0h， 以817 mg的产率得到tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate
  参考文献：
  名称：

  Hydroxylysine containing glycoconjugates: an efficient synthesis of natural galactosylhydroxylysine (Gal-Hyl) and glucosylgalactosylhydroxylysine (Glu-Gal-Hyl) and of their (5S)-epimers

  摘要：

  The paper reports the first chemical synthesis of alpha-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-5-O-hydroxylysine, a biological marker of bone resorption and of its unnatural (5S)-epimer, starting from commercial sugars and amino acids. Moreover, the synthetic protocol set-up has resulted in a new procedure for the synthesis of the beta-D-galactopyranosyl-5-O-hydroxylysine and its unnatural (5S)-epimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.006

文献信息

• Hydroxylysine containing glycoconjugates: an efficient synthesis of natural galactosylhydroxylysine (Gal-Hyl) and glucosylgalactosylhydroxylysine (Glu-Gal-Hyl) and of their (5S)-epimers
  作者：Pietro Allevi、Rita Paroni、Andrea Ragusa、Mario Anastasia

  DOI：10.1016/j.tetasy.2004.08.006

  日期：2004.10

  The paper reports the first chemical synthesis of alpha-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-5-O-hydroxylysine, a biological marker of bone resorption and of its unnatural (5S)-epimer, starting from commercial sugars and amino acids. Moreover, the synthetic protocol set-up has resulted in a new procedure for the synthesis of the beta-D-galactopyranosyl-5-O-hydroxylysine and its unnatural (5S)-epimer. (C) 2004 Elsevier Ltd. All rights reserved.