3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 229954-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 229954-84-1
• 化学式: C₈₀H₈₇N₃O₁₇
• 分子量: 1362.58
• InChiKey: URAXJFJGZNABML-MMIPVKHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.39
• 重原子数：
  100.0
• 可旋转键数：
  35.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  213.51
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到3-azidopropyl 2,6-di-O-benzyl-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

  摘要：

  Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1 -->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1 --> 3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00018-x
• 作为产物：
  描述：

  3-azidopropyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.5h， 生成 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

  摘要：

  Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1 -->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1 --> 3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00018-x