O-((3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->6)-(3-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine benzyl ester | 1381864-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: O-((3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->6)-(3-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine benzyl ester
• CAS: 1381864-63-6
• 化学式: C₄₈H₄₉N₇O₁₅
• 分子量: 963.955
• InChiKey: FNCLEDXOKLJEFB-XBKMSNQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  70.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  290.36
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为产物：
  描述：

  Fmoc-O-苄基-L-丝氨酸 在 四氢呋喃 、 三氟甲磺酸三甲基硅酯 、 水 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 57.5h， 生成 O-((3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-(1->6)-(3-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine benzyl ester 、 O-((3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->6)-(3-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl))-N-(9-fluorenylmethoxycarbonyl)-L-serine benzyl 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