D-erythritolyl-3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside | 1415556-55-6

• 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: D-erythritolyl-3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside
• 英文别名: D-erythritol-4-yl 3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside；[(2R,3S,4S,5R,6R)-4,5-di(hexanoyloxy)-6-(hexanoyloxymethyl)-2-[(2R,3S)-2,3,4-trihydroxybutoxy]oxan-3-yl] octanoate
• CAS: 1415556-55-6
• 化学式: C₃₆H₆₄O₁₃
• 分子量: 704.896
• InChiKey: ASGXVMSQMGKCMZ-PDVKCWSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  49
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-erythritol-4-yl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 水 、 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.67h， 生成 D-erythritolyl-3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside
  参考文献：
  名称：

  Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain

  摘要：

  Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca2+ signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.079