dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside phosphate | 471930-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside phosphate
• 英文别名: [(2S,3R,4S,5S,6R)-2-dibutoxyphosphoryloxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl] 4-oxopentanoate
• CAS: 471930-55-9
• 化学式: C₄₀H₅₃O₁₁P
• 分子量: 740.828
• InChiKey: HGLWJHVXYDJGEL-KDSZZTFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside phosphate 、 n-pentenyl 3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 n-pentenyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 、 n-pentenyl 2,4,6-tribenzyl-3-levulinoyl-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：

  (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol 在 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 达卡巴嗪 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成 dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside 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+

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.