O-((2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine | 188245-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-((2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine
• CAS: 188245-78-5
• 化学式: C₅₀H₅₃N₃O₁₆
• 分子量: 951.981
• InChiKey: LRXKKKRJKXCRPN-GBAFMYFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  69.0
• 可旋转键数：
  14.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  233.97
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  O-((2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以82%的产率得到O-((2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine
  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