6-(N-benzyloxycarbonylamino)hexyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 171612-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(N-benzyloxycarbonylamino)hexyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: (6-N-benzyloxycarbonylamino)hexyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside；benzyl N-[6-[[(2R,4aR,6R,7R,8R,8aS)-7-acetamido-8-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]hexyl]carbamate
• CAS: 171612-31-0
• 化学式: C₅₆H₆₆N₂O₁₂
• 分子量: 959.146
• InChiKey: SVJGDRAWCUDBGU-KDZOXRSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-(N-benzyloxycarbonylamino)hexyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 sodium cyanoborohydride 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4
• 作为产物：
  描述：

  6-(Z-氨基)-1-己醇 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 sodium methylate 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.75h， 生成 6-(N-benzyloxycarbonylamino)hexyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4

文献信息

• Synthesis of Sulfated Lex-Trisaccharides
  作者：W. Stahl、U. Sprengard、G. Kretzschmar、D. W. Schmidt、H. Kunz

  DOI：10.1002/prac.19953370196

  日期：——

  The regioselective sulfation of a Le(x)-trisaccharide having free hydroxyl groups in 2-, 3- and 4- position of the galactose elucidated their different reactivities and gave mono- and disulfated Le(x) derivatives.
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.