2,3,4-tri-O-benzyl-6-O-methyl-D-galactopyranosyl fluoride | 1092684-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-methyl-D-galactopyranosyl fluoride
• CAS: 1092684-23-5
• 化学式: C₂₈H₃₁FO₅
• 分子量: 466.55
• InChiKey: WMCHMSOHYASYLT-PBVUBXADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-6-O-methyl-D-galactopyranosyl fluoride 在 四丁基氟化铵 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranosyl)octadecane-1,3,4-triol
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.03.028
• 作为产物：
  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

文献信息

• RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines
  作者：Takuya Tashiro、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2012.05.073

  日期：2012.7

  RCAI-84, 91, and 105-108 (1–6), the analogs of KRN7000 (A) with a ureido or a thioureido linkage instead of a carboxamido bond, were synthesized to examine their immunostimulatory activity against mouse lymphocytes. According to their bioassay, the ureido analog of KRN7000 [RCAI-105 (1)] and its 6′-O-methylated derivative [RCAI-106 (4)] induced a large amount of IFN-γ in mice in vivo. The hexadecyl

  RCAI-84、91和105-108（1-6）是具有脲基或硫脲基键而不是羧酰胺键的KRN7000（A）的类似物，用于检查其对小鼠淋巴细胞的免疫刺激活性。根据他们的生物测定，KRN7000的脲基类似物[RCAI-105（1）]及其6'- O-甲基化衍生物[RCAI-106（4）]在体内小鼠体内诱导了大量的IFN-γ。十六烷基脲基类似物[RCAI-84（2）]的生物活性与KRN7000相当。辛基脲基[RCAI-107（3）]，5-苯基戊基脲基[RCAI-108（5）]和硫脲基[RCAI-91（6）]类似物几乎没有活性。
• 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.