tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate | 799267-27-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate
• 英文别名: tert-butyl (2S,5S)-6-azido-5-[(2R,3R,4S,5S,6R)-3-(2-chloroacetyl)oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 799267-27-9
• 化学式: C₄₇H₅₅ClN₄O₁₁
• 分子量: 887.427
• InChiKey: PGQMAYSFHOYXFO-UMHJTSGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  63
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate 在 palladium on activated charcoal 叔丁基二甲硅基三氟甲磺酸酯 、 zinc diacetate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (2S,5S)-2,6-diamino-5-[α-D-glucopyranosyl-(1->2)-β-D-galactopyranosyloxy]hexanoic acid ditrifluoroacetate
  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：

  3,4,6-tri-O-benzyl-2-O-chloroacetyl-D-galactopyranose 在 叔丁基二甲硅基三氟甲磺酸酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-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

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.