ethylene glycol-3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside | 1415556-60-3

• 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: ethylene glycol-3,4,6-tri-O-hexanoyl-2-O-octanoyl-β-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-di(hexanoyloxy)-6-(hexanoyloxymethyl)-2-(2-hydroxyethoxy)oxan-3-yl] octanoate
• CAS: 1415556-60-3
• 化学式: C₃₄H₆₀O₁₁
• 分子量: 644.844
• InChiKey: RZWHHCDHOWAFPO-PMILWJPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  45
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(tert-butyldimethylsiloxy)ethan-1-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 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 ethylene glycol-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

文献信息

• ANTITUMOR AGENT
  申请人：Sugiura Reiko

  公开号：US20140121175A1

  公开（公告）日：2014-05-01

  The invention is intended to provide an excellent antitumor agent. An antitumor agent contains a glycolipid glycoside compound represented by Formula (1) or a pharmacologically acceptable salt thereof as an active ingredient: in the formula, R 1 to R 4 are the same as or different from each other and represent an alkanoyl group or a hydrogen atom, and A represents a sugar alcohol residue or a polyol residue.

  该发明旨在提供一种优秀的抗肿瘤剂。一种抗肿瘤剂包含以式（1）表示的糖脂糖苷化合物或其药理学上可接受的盐作为活性成分：在该式中，R1到R4相同或不同，表示烷酰基或氢原子，A表示糖醇残基或多元醇残基。
• ANTI-TUMOR AGENT
  申请人：Kinki University

  公开号：EP2716293B1

  公开（公告）日：2017-09-06
• US9828406B2
  申请人：——

  公开号：US9828406B2

  公开（公告）日：2017-11-28
• 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
  作者：Nozomi Tsutsui、Genzoh Tanabe、Nao Morita、Yoshitomo Okayama、Ayako Kita、Reiko Sugiura、Osamu Muraoka

  DOI：10.1016/j.bmc.2015.03.079

  日期：2015.7

  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.