(2S,3S,4R)-1-O-(α-D-galctopyranosyl)-16-methyl-2--1,3,4-heptadecanetriol | 148766-51-2

• 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: (2S,3S,4R)-1-O-(α-D-galctopyranosyl)-16-methyl-2--1,3,4-heptadecanetriol
• 英文别名: agelasphin-9b；AGL-9b；(2R)-N-[(2S,3S,4R)-3,4-dihydroxy-16-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptadecan-2-yl]-2-hydroxytetracosanamide
• CAS: 148766-51-2
• 化学式: C₄₈H₉₅NO₁₀
• 分子量: 846.283
• InChiKey: ZFKNVPCSUNCEDZ-LXKABXHDSA-N

物化性质

• 沸点：
  946.6±65.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  59
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  189
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-O-(α-D-galctopyranosyl)-16-methyl-2--1,3,4-heptadecanetriol 在 吡啶 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 19.5h， 生成 2-acetoamino-1,3,4-tri-O-acetyl-16-methyl-1,3,4-hexadecanetriol
  参考文献：
  名称：

  Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus

  摘要：

  New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic ol-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.

  DOI：

  10.1016/s0040-4020(01)86991-x
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2S,3S,4R)-1-O-(α-D-galctopyranosyl)-16-methyl-2--1,3,4-heptadecanetriol
  参考文献：
  名称：

  Synthesis and stereochemistry of agelasphin-9b

  摘要：

  Agelasphin-9b, one of the alpha-galactosylceramides from an Okinawan marine sponge, was synthesized, and the absolute stereochemistry was determined.

  DOI：

  10.1016/s0040-4039(00)73890-1

文献信息

• Hexosylceramides as adjuvants and their uses in pharmaceutical compositions
  申请人：GBF-GESELLSCHAFT FÜR BIOTECHNOLOGISCHE FORSCHUNG MBH

  公开号：EP1776963A1

  公开（公告）日：2007-04-25

  The present invention relates to new adjuvants and the uses in pharmaceutical compositions, like in vaccines. In particular, the present invention provides new compounds useful as adjuvants for prophylactic and/or therapeutic vaccination in the treatment of infectious diseases, inflammatory diseases, autoimmune diseases, tumours, allergies as well as for the control of fertility in human or animal populations. The compounds are particularly useful not only as systemic, but preferably as mucosal adjuvants. In addition, the invention relates to its uses as active ingredients in pharmaceutical compositions.

  本发明涉及新的佐剂及其在制备药物组合物中的应用，例如在疫苗中的应用。特别地，本发明提供了新的化合物，可用作预防性和/或治疗性疫苗中的佐剂，用于治疗传染性疾病、炎症性疾病、自身免疫性疾病、肿瘤、过敏以及在人类或动物群体中控制生育。这些化合物不仅特别适用于系统性，而且更适用于黏膜佐剂。此外，本发明还涉及其作为制药组合物中的活性成分的用途。
• HEXOSYLCERAMIDES AS ADJUVANTS AND THEIR USES IN PHARMACEUTICAL COMPOSITIONS
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP1940464B1

  公开（公告）日：2009-07-22
• Hexosylceramides as Adjuvants and Their Uses in Pharmaceutical Compositions
  申请人：Ebensen Thomas

  公开号：US20080206319A1

  公开（公告）日：2008-08-28

  The present invention relates to new adjuvants and the uses in pharmaceutical compositions, like in vaccines. In particular, the present invention provides new compounds useful as adjuvants for prophylactic and/or therapeutic vaccination in the treatment of infectious diseases, inflammatory diseases, autoimmune diseases, tumours, allergies as well as for the control of fertility in human or animal populations. The compounds are particularly useful not only as systemic, but preferably as mucosal adjuvants. In addition, the invention relates to its uses as active ingredients in pharmaceutical compositions.
• US5780441A
  申请人：——

  公开号：US5780441A

  公开（公告）日：1998-07-14
• US8053417B2
  申请人：——

  公开号：US8053417B2

  公开（公告）日：2011-11-08