thexyldimethylsilyl β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside | 320351-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thexyldimethylsilyl β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6R)-3-azido-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 320351-44-8
• 化学式: C₂₀H₃₉N₃O₁₀Si
• 分子量: 509.629
• InChiKey: YHDBRYNOZYCVSQ-CPIZOFMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  173
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside 在 lipase from Candida antarctica 、 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 24.5h， 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
• 作为产物：
  描述：

  thexyldimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到thexyldimethylsilyl β-D-galactopyranosyl-(1->3)-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

文献信息

• Regioselective lipase acylation as a useful tool for separation and selective protection of β-d-Gal(1→4)-d-GlcNAc and β-d-Gal(1→3)-d-GlcNAc disaccharides
  作者：Barbara La Ferla、Luigi Lay、Giovanni Russo、Luigi Panza

  DOI：10.1016/s0957-4166(00)00342-6

  日期：2000.9

  Supported lipase from Candida antarctica (Chirazyme((R))) was employed for a regioselective protection of the 2-azido derivatives 1 and 2, synthetic equivalents of beta-(D)-Gal(1 ->3)-(D)-GlcNAc and beta-(D)-Gal(1->4)-(D-)GlcNAc (N-acetyl lactosamine), respectively. The selectivity of the enzyme towards 1 and 2 was also exploited for an easy separation of the mixture of the two compounds obtained from a straightforward synthetic approach. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series
  作者：Barbara La Ferla、Davide Prosperi、Luigi Lay、Giovanni Russo、Luigi Panza

  DOI：10.1016/s0008-6215(02)00164-7

  日期：2002.9

  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.