dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate | 471930-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate
• 英文别名: [(2S,3R,4R,5R,6R)-2-dibutoxyphosphoryloxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl] acetate
• CAS: 471930-56-0
• 化学式: C₃₂H₄₃Cl₃NO₁₀P
• 分子量: 739.027
• InChiKey: TZZUPZNKAKQYPG-RLXMVLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate 、 n-pentenyl 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 0.5h， 以93%的产率得到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
  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：

  3-O-Acetyl-4,6-di-O-benzyl-D-galactal 在 sodium tetrahydroborate 、 sodium azide 、 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 nickel dichloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 54.33h， 生成 dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate
  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+