tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate | 799267-28-0

• 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-β-D-galactopyranosyloxy)hexanoate
• 英文别名: tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)hexanoate；tert-butyl (2S,5S)-6-azido-5-[(2R,3R,4R,5S,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 799267-28-0
• 化学式: C₄₅H₅₄N₄O₁₀
• 分子量: 810.945
• InChiKey: ZOYUKUJSOHZCSI-CCAPTLSCSA-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,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate 在 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 为溶剂， 反应 2.0h， 生成 tert-butyl (2S,5S)-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
• 作为产物：
  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 zinc diacetate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以91%的产率得到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