tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate | 726173-68-8

• 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,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate
• 英文别名: tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)hexanoate；tert-butyl (2S,5R)-6-azido-5-[(2R,3R,4R,5S,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 726173-68-8
• 化学式: C₄₅H₅₄N₄O₁₀
• 分子量: 810.945
• InChiKey: ZOYUKUJSOHZCSI-ZBPZARJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  59
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 (2S,5R)-2,6-diamino-5-(β-D-galactopyranosyloxy)hexanoic acid bistrifluoroacetate
  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-1,2-O-dichloroacetyl-D-galactopyranose 在 ammonium hydroxide 、 叔丁基二甲硅基三氟甲磺酸酯 、 zinc diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate
  参考文献：
  名称：

  葡萄糖基半乳糖基羟基赖氨酸（Glu-Gal-Hyl）的首次合成，这是胶原蛋白更新的重要生物学指标。

  摘要：

  本文报道了从商业化合物开始的首次化学合成α-D-吡喃葡萄糖基-（1-> 2）-β-D-吡喃半乳糖基-O-羟基赖氨酸的过程，羟基赖氨酸的糖苷对皮肤和骨骼胶原蛋白的更新具有重要的指示作用。

  DOI：

  10.1016/j.bmcl.2004.03.068

文献信息

• Total synthesis of the collagen glycosylated cross-link β-d-galactopyranosyl-O-pyridinoline and of its unnatural epimer β-d-galactopyranosyl-O-epipyridinoline
  作者：Pietro Allevi、Raffaele Colombo、Elios Giannini、Mario Anastasia

  DOI：10.1016/j.tetasy.2007.07.006

  日期：2007.7

  A short parallel synthesis Of beta-D-galactopyranosyl-O-pyridinoline (Ga1-PYD), a collagen glycoconjugated cross-link, and of Ga1-epiPYD, a (5S)-epimer, useful as internal standard in the analytical evaluation of the natural isomer in human tissue, is reported. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.
• The first synthesis of glucosylgalactosyl hydroxylysine (Glu-Gal-Hyl) an important biological indicator of collagen turnover
  作者：Pietro Allevi、Mario Anastasia、Rita Paroni、Andrea Ragusa

  DOI：10.1016/j.bmcl.2004.03.068

  日期：2004.6

  This paper reports the first chemical synthesis of alpha-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-O-hydroxylysine, a glycoside of hydroxylysine important as indicator of skin and bone collagen turnover, starting with commercial compounds.

  本文报道了从商业化合物开始的首次化学合成α-D-吡喃葡萄糖基-（1-> 2）-β-D-吡喃半乳糖基-O-羟基赖氨酸的过程，羟基赖氨酸的糖苷对皮肤和骨骼胶原蛋白的更新具有重要的指示作用。