Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-SPh | 239466-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-SPh
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 239466-02-5
• 化学式: C₄₄H₅₇NO₂₄S
• 分子量: 1015.99
• InChiKey: MDMYILVYKXRUPB-LMRCHRCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  70
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  337
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-SPh 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 水 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

  摘要：

  Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00930-2
• 作为产物：
  描述：

  乙酸酐 、 Gal(b1-4)GlcNAc(b1-2)Man(a)-SPh 在 吡啶 作用下， 以83%的产率得到Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-SPh
  参考文献：
  名称：

  The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

  摘要：

  Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00930-2