hexadecyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside | 263759-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexadecyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6R)-6-hexadecoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 263759-03-1
• 化学式: C₅₈H₇₃Cl₄NO₁₆
• 分子量: 1182.03
• InChiKey: RTHRWLFWPFLKAP-TUIGDTDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  79
• 可旋转键数：
  35
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  hexadecyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 22.0h， 以73%的产率得到(2S,3R,4S,5R,6R)-2-((2R,3S,4R,5R,6R)-5-Amino-4-benzyloxy-2-benzyloxymethyl-6-hexadecyloxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid

  摘要：

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

  DOI：

  10.1080/07328300008544063
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 2,4,6-三甲基吡啶 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 hexadecyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid

  摘要：

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

  DOI：

  10.1080/07328300008544063