tert-butyl (2S,5R)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate | 953073-37-5

• 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-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate
• 英文别名: tert-butyl (2S,5R)-6-amino-2-[benzyl(phenylmethoxycarbonyl)amino]-5-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 953073-37-5
• 化学式: C₅₉H₆₈N₂O₁₀
• 分子量: 965.196
• InChiKey: KFUIARDFMXFGCV-WNNLLCLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  71
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5R)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate 、 (S)-6-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester 在 sodium carbonate 、 氧气 作用下， 以 乙腈 、 甲醇 为溶剂， 20.0 ℃ 、131.73 kPa 条件下， 反应 174.0h， 以61%的产率得到1-[(2R,5S)-5-[benzyl(phenylmethoxycarbonyl)amino]-6-[(2-methylpropan-2-yl)oxy]-6-oxo-2-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexyl]-5-[(3S)-4-[(2-methylpropan-2-yl)oxy]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutyl]-4-[(2S)-3-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]pyridin-1-ium-3-olate
  参考文献：
  名称：

  Total synthesis of the collagen glycosylated cross-link β-d-galactopyranosyl-O-pyridinoline and of its unnatural epimer β-d-galactopyranosyl-O-epipyridinoline

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2007.07.006
• 作为产物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 在 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基碘化铵 、 sodium hydride 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.0h， 生成 tert-butyl (2S,5R)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate
  参考文献：
  名称：

  Total synthesis of the collagen glycosylated cross-link β-d-galactopyranosyl-O-pyridinoline and of its unnatural epimer β-d-galactopyranosyl-O-epipyridinoline

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2007.07.006

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.