tert-butyl (2S,5S)-6-amino-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate | 1005413-40-0

• 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-amino-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate
• 英文别名: tert-butyl (2S,5S)-6-amino-5-[(2R,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 1005413-40-0
• 化学式: C₇₉H₉₀N₂O₁₅
• 分子量: 1307.59
• InChiKey: FZBHFDMFZXKNCH-VYRNHADYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  96
• 可旋转键数：
  38
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S)-6-amino-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]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， 反应 80.0h， 以61%的产率得到
  参考文献：
  名称：

  A simple strategy for the synthesis of the glycosylated collagen biomarkers α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-O-pyridinoline (Glc-Gal-PYD), α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their unnatural epimers Glc-Gal-epiPYD and Glc-Gal-epiHyl

  摘要：

  A short synthetic strategy for the preparation of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-O-pyridinoline (Glc-Gat-PYD), of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their respective epimers, Glc-Gal-epiPYD and Glc-Gal-epiHyl, useful for the analytical evaluation of collagen biomarkers in human sinovium and bone, is reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.037
• 作为产物：
  描述：

  tert-butyl (2S)-6-azido-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以41%的产率得到tert-butyl (2S,5S)-6-amino-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate
  参考文献：
  名称：

  A simple strategy for the synthesis of the glycosylated collagen biomarkers α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-O-pyridinoline (Glc-Gal-PYD), α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their unnatural epimers Glc-Gal-epiPYD and Glc-Gal-epiHyl

  摘要：

  A short synthetic strategy for the preparation of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-O-pyridinoline (Glc-Gat-PYD), of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their respective epimers, Glc-Gal-epiPYD and Glc-Gal-epiHyl, useful for the analytical evaluation of collagen biomarkers in human sinovium and bone, is reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.037