Acetic acid (3aR,4S,6S,7S,7aR)-6-[(3aR,4S,6R,7S,7aR)-6-(4-isothiocyanato-butoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester | 214078-28-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (3aR,4S,6S,7S,7aR)-6-[(3aR,4S,6R,7S,7aR)-6-(4-isothiocyanato-butoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
• CAS: 214078-28-1
• 化学式: C₂₅H₃₉NO₁₀S
• 分子量: 545.651
• InChiKey: MBTKXYPTYQFQGH-GNUNUEAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  112.5
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  三(2-氨基乙基)胺 、 Acetic acid (3aR,4S,6S,7S,7aR)-6-[(3aR,4S,6R,7S,7aR)-6-(4-isothiocyanato-butoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到tris[2-[thioureylenebutyl 2-O-acetyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-fucopyranoside]ethyl]amine
  参考文献：
  名称：

  The Syntheses of δ-NCS-Butyl α-l-Fucosides and Fucobiosides and Their Clustering to Traintennary Glycomimetics

  摘要：

  L-Fucose is an especially important monosaccharide constituent in eukaryotic glycoconjugates. Its recognition by fucose specific lectins might play an important role in embryonic development, cancer development and metastasis. Therefore it is of great interest to develop potent inhibitors of fucose specific lectins, both to investigate as well as to manipulate the respective interactions. A promising approach to high affinity fucoside ligands is the synthesis of oligovalent fucosyl clusters. The synthesis of isothiocyanato-functionalized spacer alpha-fucosides and fucobiosides is described together with their clustering on tris(2-aminoethyl)amine giving rise to the first thiourea bridged cluster fucosides 14 and 16 in excellent yields.

  DOI：

  10.1080/07328309808001889
• 作为产物：
  描述：

  Acetic acid (3aR,4S,6S,7S,7aR)-6-[(3aR,4S,6R,7S,7aR)-6-(4-chloro-butoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 sodium azide 、 1,1,3,3-四甲基脲 、 亚磷酸三乙酯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.0h， 生成 Acetic acid (3aR,4S,6S,7S,7aR)-6-[(3aR,4S,6R,7S,7aR)-6-(4-isothiocyanato-butoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  The Syntheses of δ-NCS-Butyl α-l-Fucosides and Fucobiosides and Their Clustering to Traintennary Glycomimetics

  摘要：

  L-Fucose is an especially important monosaccharide constituent in eukaryotic glycoconjugates. Its recognition by fucose specific lectins might play an important role in embryonic development, cancer development and metastasis. Therefore it is of great interest to develop potent inhibitors of fucose specific lectins, both to investigate as well as to manipulate the respective interactions. A promising approach to high affinity fucoside ligands is the synthesis of oligovalent fucosyl clusters. The synthesis of isothiocyanato-functionalized spacer alpha-fucosides and fucobiosides is described together with their clustering on tris(2-aminoethyl)amine giving rise to the first thiourea bridged cluster fucosides 14 and 16 in excellent yields.

  DOI：

  10.1080/07328309808001889