2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose
• 英文别名: 2,3,4-tri-O-benzyl-6-O-methyl-D-galactopyranose；2,3,4-tri-O-benzyl-6-O-methyl-α,β-D-galactopyranose；(3R,4S,5S,6R)-6-(methoxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-ol
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: FLJUYHZJTGMKJJ-PBVUBXADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到2,3,4-tri-O-benzyl-6-O-methyl-D-galactopyranosyl fluoride
  参考文献：
  名称：

  NOVEL GLYCOLIPID AND USE THEREOF

  摘要：

  公开号：

  EP2272854B1
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 硫酸 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 生成 2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose
  参考文献：
  名称：

  ESTERIFIED ALPHA-GALACTOSYLCERAMIDE

  摘要：

  该发明提供了用于癌症治疗等的酯化α-半乳糖鞘氨醇，以及含有该酯化物的药物。具体来说，该发明涉及一种由以下式表示的化合物（I）： 其中R1是具有1至30个碳原子数的烃基，R2是具有1至20个碳原子数的烃基，R3是氢原子或具有1至5个碳原子数的烃基，R4和R5相同或不同，每个都是氢原子或具有1至5个碳原子数的烃基，或者R4和R5结合在一起形成具有1至5个碳原子数的二价烃基，且可选择地与邻近的乙二醚氧形成环结构，或其盐。

  公开号：

  US20110224158A1

文献信息

• Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)
  作者：Masao Shiozaki、Takuya Tashiro、Hiroyuki Koshino、Ryusuke Nakagawa、Sayo Inoue、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.carres.2010.05.003

  日期：2010.8

  (alphaGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in alphaGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNgamma

  α-半乳糖苷神经酰胺（alphaGalCer，KRN7000）由于具有结合CD1d分子介导的iNKT细胞的能力，已被鉴定为免疫过程的调节剂。从d-阿拉伯糖醇或l-核糖合成了alphaGalCer中的酰胺基被酯或醚基取代时的一些类似物，以评估其激活iNKT细胞的能力。酯类似物30a，31a和61显示出对iNKT细胞产生IFNγ和IL-4的活性，而α-半乳糖基神经酰胺的醚（31b）和4-甲氧基酯（76）类似物对iNKT细胞没有活性。
• ESTERIFIED ALPHA-GALACTOSYLCERAMIDE
  申请人：Riken

  公开号：EP2336144B1

  公开（公告）日：2015-01-21
• RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tetlet.2008.09.074

  日期：2008.11

  RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
• RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2013.03.028

  日期：2013.6

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.
• US8580751B2
  申请人：——

  公开号：US8580751B2

  公开（公告）日：2013-11-12