thexyldimethylsilyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside | 483278-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: thexyldimethylsilyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
• CAS: 483278-47-3
• 化学式: C₂₇H₄₇N₃O₁₂Si
• 分子量: 633.769
• InChiKey: OOPZPDJVZBSJRW-XOYRTLCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  197.2
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl trichloroacetimidate 、 thexyldimethylsilyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以91%的产率得到thexyldimethylsilyl 3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl-(1->2)-6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-[3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl-(1->4)]-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series

  摘要：

  The synthesis of protected fucosylated derivatives of a Gal beta(1--> 3)GlcNAc and of lactosamine Galbeta(1--> 4)GlcNAc building blocks contained in human milk oligosaccharides is described. Both chemical and enzymatic methods have been exploited for selective protection of the disaccharide. Fucosylation of the appropriate derivatives allowed an easy and relatively short access to different products from common precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00164-7
• 作为产物：
  描述：

  thexyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 lipase from Candida antarctica 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.42h， 生成 thexyldimethylsilyl 6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series

  摘要：

  The synthesis of protected fucosylated derivatives of a Gal beta(1--> 3)GlcNAc and of lactosamine Galbeta(1--> 4)GlcNAc building blocks contained in human milk oligosaccharides is described. Both chemical and enzymatic methods have been exploited for selective protection of the disaccharide. Fucosylation of the appropriate derivatives allowed an easy and relatively short access to different products from common precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00164-7