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 | 471930-64-0

• 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: 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
• 英文别名: [(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-5-(2,2-dimethylpropanoyloxy)-6-[(2R,3R,4S,5R,6R)-5-(2,2-dimethylpropanoyloxy)-6-pent-4-enoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl] 4-oxopentanoate
• CAS: 471930-64-0
• 化学式: C₈₇H₁₀₄O₂₀
• 分子量: 1469.77
• InChiKey: BKMUPHSHACLNSA-ORJXEGQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  107
• 可旋转键数：
  44
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  216
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  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 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  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：

  2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate 、 n-pentenyl 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 40.0h， 以54%的产率得到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+

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.