3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-sulfo-α-D-glucopyranosyl>-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol sodium salt | 137895-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-sulfo-α-D-glucopyranosyl>-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol sodium salt
• 英文别名: sodium;[(2S,3S,4S,5R,6S)-6-[(2S)-2-hexadecanoyloxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxypropoxy]-3,4,5-tris[(4-methoxyphenyl)methoxy]oxan-2-yl]methanesulfonate
• CAS: 137895-69-3
• 化学式: C₆₇H₉₉O₁₅S*Na
• 分子量: 1199.57
• InChiKey: MWVPFGCPJCMILA-VDHMYIQLSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  11.58
• 重原子数：
  84
• 可旋转键数：
  49
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  192
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-sulfo-α-D-glucopyranosyl>-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol sodium salt 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以70%的产率得到3-O-(6-deoxy-6-sulfo-α-D-glucopyranosyl)-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol sodium salt
  参考文献：
  名称：

  Synthesis of a cyanobacterial sulfolipid: confirmation of its structure, stereochemistry and anti-HIV-1 activity

  摘要：

  The total synthesis of a cyanobacterial sulfolipid is described. The key steps involve the epoxidation of a glycal followed by conversion to a 1-beta-fluoro-2-alpha-hydroxy moiety. After protection of the alcohol, the anomeric beta-fluoro substituent is used to fashion an alpha-glycoside of a glycerol. A sulfonic acid is introduced at the 6-position by oxidation of a thioacetate with Oxone in the presence of a triene subunit.

  DOI：

  10.1021/ja00028a036