benzyl (2S)-3-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-[[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate | 1381864-67-0

• 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: benzyl (2S)-3-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-[[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 1381864-67-0
• 化学式: C₄₇H₅₁N₇O₁₈
• 分子量: 1001.96
• InChiKey: SVVRKLICALSHHA-APHBGIQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  72
• 可旋转键数：
  27
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  262
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-3-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-[[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.33h， 生成 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->6)-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-(fluorenylmethyloxycarbonyl)-L-serine tert-butyl ester
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(3-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 在 吡啶 、 高氯酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 benzyl (2S)-3-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-[[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059