(2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid | 309928-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid
• 英文别名: (2S,5S)-6-azido-5-hydroxy-2-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 309928-97-0
• 化学式: C₁₄H₁₈N₄O₅
• 分子量: 322.321
• InChiKey: VDYWDSMEIZXJRC-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 在 三氟乙酸 作用下， 反应 0.17h， 以100%的产率得到(2S,5S)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone
  参考文献：
  名称：

  Synthesis of all four possible stereoisomers of 5-hydroxylysine

  摘要：

  A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00281-0
• 作为产物：
  描述：

  (S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone 在 sodium tetrahydroborate 、 sodium azide 、 phosphate buffer pH 7.4 、 氢溴酸 、 碳酸氢钠 、 三氟乙酸 、 α-chymotrypsin 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 14.17h， 生成 (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid
  参考文献：
  名称：

  Synthesis of all four possible stereoisomers of 5-hydroxylysine

  摘要：

  A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00281-0

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.
• Synthesis of all four possible stereoisomers of 5-hydroxylysine
  作者：Pietro Allevi、Mario Anastasia

  DOI：10.1016/s0957-4166(00)00281-0

  日期：2000.8

  A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. (C) 2000 Elsevier Science Ltd. All rights reserved.