Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester | 188302-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• CAS: 188302-07-0
• 化学式: C₂₈H₃₆Cl₃NO₁₈
• 分子量: 780.949
• InChiKey: UEQKUPGAPOZESQ-PQYWDRMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 钯 molecular sieve 、 三氟甲磺酸 、 氢气 、 sodium methylate 、 乙二胺 作用下， 以 正丁醇 为溶剂， 反应 12.25h， 生成 线性B三糖
  参考文献：
  名称：

  Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.

  摘要：

  Gal alpha 1-3Gal-pNP was prepared enzymatically from Gal-pNP using alpha-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Gal alpha 1-3Gal-PEG conjugate. After removing the pNP group in Gal alpha 1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Gal alpha 1-3Gal beta 1-4GlcNAc and corresponding trisaccharide-PEG conjugate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00017-6
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 在 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.5h， 生成 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.

  摘要：

  Gal alpha 1-3Gal-pNP was prepared enzymatically from Gal-pNP using alpha-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Gal alpha 1-3Gal-PEG conjugate. After removing the pNP group in Gal alpha 1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Gal alpha 1-3Gal beta 1-4GlcNAc and corresponding trisaccharide-PEG conjugate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00017-6

文献信息

• Synthesis of a pentasaccharide and a heptasaccharide corresponding to an ovarian glycoprotein; studies towards glycosylations
  作者：Nynke M. Spijker、Pieter Westerduin、Constant A.A. van Boeckel

  DOI：10.1016/s0040-4020(01)88221-1

  日期：1992.1

  O-glycoprotein, are presented. The protected pentasaccharide 1 was prepared by condensing a trisaccharide donor 18c with a disaccharide acceptor (8b, while condensation of the same trisaccharide donor (18c) with a tetrasaccharide acceptor (25b) provided the protected heptasaccharide 2. Special attention was paid to the deblocking of the protected derivatives 1 and 2 to give I and II, respectively. The β-bonds

  介绍了对应于卵巢O-糖蛋白的五糖I和七糖II的合成。受保护的五糖1是通过将三糖供体18c与二糖受体（8b）缩合而制备的，而相同的三糖供体（18c）与四糖受体（25b）的缩合则提供了受保护的七糖2，特别要注意的是被保护的衍生物1和2，得到我和II，分别在所述的β-键8b中通过使用在C-2具有非参与基团的糖基供体来制备Ab和25b，这些糖基供体较早用于合成α-糖苷。为了合成三糖供体（18c），比较了几种活化的Galα（1-> 3）Gal二糖与受保护的GlcNAc残基的缩合。已发现α/β比和该糖基化的产率受异头中心的离去基团，参与的酰基的特性，特别是受主与受主之间不利的空间相互作用的影响。为了减少供体和受体之间的这种空间相互作用，将GlcNAc受体的构象更改为1,6-脱水衍生物16，这提供了与糖基溴13c糖基化的高产所需的三糖17。
• Stereoselective Synthesis of the Gal‐α‐(1→3)‐Gal‐β‐(1→3)‐GlcNAc Trisaccharide: a new Ligand for DCAR and Mincle C‐Type Lectin Receptors
  作者：Jacopo Tricomi、Mike Aoun、Bingze Xu、Rikard Holmdahl、Barbara Richichi

  DOI：10.1002/cbic.202400026

  日期：2024.5.2

  The identification and synthesis of a new ligand for two C-type lectin receptors, i. e. dendritic cell activating receptor (DCAR) and macrophage-inducible C-type lectin (Mincle), are described.

  两种C型凝集素受体的新配体的鉴定和合成，即。 e .描述了树突细胞激活受体 (DCAR) 和巨噬细胞诱导型 C 型凝集素 (Mincle)。