4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside | 187173-16-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside
• CAS: 187173-16-6
• 化学式: C₂₆H₃₁N₃O₆
• 分子量: 481.549
• InChiKey: UBPMVRFIYHTXFN-XRKIENNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  111.98
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 (2S,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  New synthetic trisaccharide inhibitors for N-acetylglucosaminyltransferase-V

  摘要：

  The trisaccharide octyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-beta-D-glucopyranoside (5) is an acceptor substrate for N-acetylglucosaminyltransferase-V (EC 2.4.1.155) which adds a beta-GlcNAc residue to OH-6 of the central Man-residue. In the present work, 10 analogues of 5, each missing the potentially reactive OH-6 group, were chemically synthesized. The key intermediate used was octyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->2)-6-amino-6-deoxy-4-O-methyl-alpha-D-mannopyranosyl-(1-->6)-beta-D-glucopyranoside (6a), which was synthesized in stepwise fashion by sequential coupling of protected monosaccharide residues. The 6'-amino group in 6a, was then selectively derivatized by either acylation or alkylation with hydrophobic, hydrophilic, charged, aromatic and potential covalently inactivating groups. The 10 trisaccharide analogues thus produced were evaluated for inhibition against GlcNAcT-V isolated from hamster kidney. All of the compounds were competitive inhibitors with K-i values ranging from 21 to 297 mu M. These results indicate that acceptor substrate (or inhibitor)-enzyme complex does not involve critical recognition contacts at the position of transfer. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00180-0
• 作为产物：
  描述：

  4-pentenyl 4,6-O-(4-methoxybenzylidene)-α-D-mannopyranoside 在 吡啶 、 sodium azide 、 3 A molecular sieve 、 sodium hydride 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.33h， 生成 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  New synthetic trisaccharide inhibitors for N-acetylglucosaminyltransferase-V

  摘要：

  The trisaccharide octyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-beta-D-glucopyranoside (5) is an acceptor substrate for N-acetylglucosaminyltransferase-V (EC 2.4.1.155) which adds a beta-GlcNAc residue to OH-6 of the central Man-residue. In the present work, 10 analogues of 5, each missing the potentially reactive OH-6 group, were chemically synthesized. The key intermediate used was octyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->2)-6-amino-6-deoxy-4-O-methyl-alpha-D-mannopyranosyl-(1-->6)-beta-D-glucopyranoside (6a), which was synthesized in stepwise fashion by sequential coupling of protected monosaccharide residues. The 6'-amino group in 6a, was then selectively derivatized by either acylation or alkylation with hydrophobic, hydrophilic, charged, aromatic and potential covalently inactivating groups. The 10 trisaccharide analogues thus produced were evaluated for inhibition against GlcNAcT-V isolated from hamster kidney. All of the compounds were competitive inhibitors with K-i values ranging from 21 to 297 mu M. These results indicate that acceptor substrate (or inhibitor)-enzyme complex does not involve critical recognition contacts at the position of transfer. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00180-0