O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate | 1201598-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate
• 英文别名: 2,3-di-O-benzyl-4,6-O-benzylidene-1-O-trichloroacetimidoyl-α/β-D-galactopyranoside
• CAS: 1201598-10-8
• 化学式: C₂₉H₂₈Cl₃NO₆
• 分子量: 592.903
• InChiKey: RUWQCKVLXFTLBX-DVPQLLMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  79.23
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.83h， 生成
  参考文献：
  名称：

  希瓦氏菌日本型菌株 KMM 3299T 的可缀合四糖重复单元的全合成

  摘要：

  在这里，我们报告了希瓦氏菌日本型菌株 KMM 3299 T的可缀合四糖重复单元的首次全合成。稀有脱氧氨基糖的存在以及三个连续 1,2-顺式糖苷键的安装使得合成变得非常困难。通过使用半乳糖醛酸供体克服了具有挑战性的后期氧化。从d-甘露糖开始，通过 22 个步骤的最长线性序列完成全合成，总产率为 3.5%。

  DOI：

  10.1021/acs.orglett.4c01354
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  肺炎链球菌两性离子多糖Sp1重复单元的全合成

  摘要：

  本文报道了肺炎链球菌两性离子多糖 Sp1的三糖重复单元的全合成，该多糖 Sp1 含有稀有糖、2-乙酰氨基-4-氨基-2,4,6-三聚氧-d-半乳糖 (AAT) 和三个连续的 1， 2-顺式-糖苷键。全合成通过高度立体选择性糖基化和后期氧化作为关键步骤完成，涉及最长的 21 步线性序列，总产率为 4.4%。

  DOI：

  10.1021/acs.joc.1c02409

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。
• Glycosylation Catalyzed by a Chiral Brønsted Acid
  作者：Daniel J. Cox、Martin D. Smith、Antony J. Fairbanks

  DOI：10.1021/ol1001895

  日期：2010.4.2

  The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochemical outcome of the glycosylation processes, hinting that perhaps diastereocontrol of glycosylation processes may become achievable through the judicious use of chiral organic catalysts.
• Introduction of aromatic group on 4′-OH of α-GalCer manipulated NKT cell cytokine production
  作者：Wenpeng Zhang、Chengfeng Xia、Janos Nadas、Wenlan Chen、Li Gu、Peng George Wang

  DOI：10.1016/j.bmc.2010.11.061

  日期：2011.4

  The glycosphingolipid alpha-GalCer has been found to influence mammalian immune system significantly through the natural killer T cells. Unfortunately, the pre-clinical and clinical studies revealed several critical disadvantages that prevented the therapeutic application of alpha-GalCer in treating cancer and other diseases. Recently, the detailed illustration of the CD1d/alpha-GalCer/NKT TCR complex crystal structural, together with other latest structural and biological understanding on glycolipid ligands and NKT cells, provided a new platform for developing novel glycolipid ligands with optimized therapeutic effects. Here, we designed a series of novel aromatic group substituted alpha-GalCer analogues. The biological activity of these analogues was characterized and the results showed the unique substitution group manipulated the immune responses of NKT cells. Computer modeling and simulation study indicated the analogues had unique binding mode when forming CD1d/glycolipid/NKT TCR complex, comparing to original alpha-GalCer. (C) 2010 Published by Elsevier Ltd.