n-pentenyl 4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside | 471930-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-pentenyl 4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-3-(2,2-dimethylpropanoyloxy)-5-[(2R,3R,4S,5S,6R)-4-[(2S,3R,4R,5R,6R)-4-hydroxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-pent-4-enoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 471930-72-0
• 化学式: C₁₀₄H₁₂₀Cl₃NO₂₃
• 分子量: 1858.45
• InChiKey: HLIZNEQDXMTDCF-WYAIRFGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  131
• 可旋转键数：
  49
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  259
• 氢给体数：
  2
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl) phosphate 、 n-pentenyl 4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以88%的产率得到n-pentenyl 2-acetyl-3,4,6-tribenzyl-β-D-Galp-(1->3)-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-Galp-(1->3)-2,4,6-tribenzyl-α-D-Galp-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-Galp-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+
• 作为产物：
  描述：

  n-pentenyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到n-pentenyl 4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+

文献信息

• Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3
  作者：Folkert Bosse、Lisa A. Marcaurelle、Peter H. Seeberger

  DOI：10.1021/jo025834+

  日期：2002.9.1

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.