thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside | 320351-47-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-5-azido-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-hydroxyoxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• CAS: 320351-47-1
• 化学式: C₂₄H₄₃N₃O₁₂Si
• 分子量: 593.704
• InChiKey: WFQZSIUEOCDBQN-PUZGNSKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl 6-O-acetyl-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 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.83h， 生成 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：

  2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 lipase from Candida antarctica 、 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 24.92h， 生成 thexyldimethylsilyl 6-O-acetyl-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

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.