2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside | 129214-38-6

• 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-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside
• 英文别名: 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranose；2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranose；[(3S,4S,5R,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 129214-38-6
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: CIYOOYKJZYSBTB-MJOWNYDZSA-N

物化性质

• 沸点：
  614.6±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside 在 二乙胺基三氟化硫 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  An anionic inositol phosphate glycan pseudotetrasaccharide exhibits high insulin-mimetic activity in rat adipocytes

  摘要：

  Inositol phosphate glycan pseudotetrasaccharides consisting of man-(alpha 1-6)-man-(alpha 1-4)-glcN-(alpha,beta l-6)-myo-inositol-1,2-cyclic phosphate possessing a sulfate group at either O-6 (compounds 3 alpha,beta) or O-2 (compounds 4 alpha,beta) of the terminal mannose have been prepared. Compound 4 alpha was able to stimulate lipogenesis in native rat adipocytes to 78% of the maximal insulin response (MIR) with an EC50 Of 1.1 mu M. The other compounds exhibited lower maximal stimulations (47-63% MIR) and higher EC50 values (9.5-10.6 mu M). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.020
• 作为产物：
  描述：

  2-methoxyethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以54%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside
  参考文献：
  名称：

  2-甲氧基乙基保护醛糖的还原羟基

  摘要：

  多种具有乙酰基或烯丙基的 D-葡萄糖、D-半乳糖、D-甘露糖、D-木糖、L-阿拉伯糖、L-岩藻糖和 L-鼠李糖的苄基化 1-OH 衍生物合成自通过在二氯甲烷中用 TiCl4 短暂处理并随后在硅胶柱上水解中间体 1-Cl 衍生物，得到相应保护的 2-甲氧基乙基糖苷。

  DOI：

  10.1246/bcsj.62.3549

文献信息

• Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor
  作者：Barbara Richichi、Lucio Luzzatto、Rosario Notaro、Giancarlo la Marca、Cristina Nativi

  DOI：10.1016/j.bioorg.2010.12.002

  日期：2011.4

  role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure–function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources; obtaining homogeneous and well-defined GPI structures by synthesis, is both a challenge and an attractive goal. We report here the convergent synthesis of the essential

  GPI锚的生物学作用至关重要。然而，我们离完全了解这些分子的结构-功能关系还很远。一个主要的限制因素是可从自然资源中获得的微量产品。通过合成获得均质且定义明确的GPI结构，既是挑战，也是诱人的目标。我们在这里报告人类GPI锚点1的基本核心的收敛合成，利用共同的前体获得三糖供体2和新的保护基序列。首次制备的最终产品具有生物活性。
• Total Synthesis of Phosphatidylinositol Mannosides of <i>Mycobacterium tuberculosis</i>
  作者：Xinyu Liu、Bridget L. Stocker、Peter H. Seeberger

  DOI：10.1021/ja0565368

  日期：2006.3.1

  The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudotrisaccharide 2, which allowed for convergent access to the glycan backbone of the phosphatidylinositol dimannoside (PIM2) and hexamannoside (PIM6)

  描述了磷脂酰肌醇甘露糖苷 (PIM) 的全合成，这是在结核分枝杆菌细胞壁上发现的一类关键抗原糖脂。合成策略依赖于四甘露糖苷 1 和假三糖 2 的 [4 + 3] 糖基化，这允许聚合访问磷脂酰肌醇二甘露糖苷 (PIM2) 和六甘露糖苷 (PIM6) 的聚糖骨架。基于铜催化的交叉偶联反应实现了结核硬脂酸的简短实用合成。聚糖和脂质部分的结合导致了天然 PIM2 和 PIM6 的首次全合成。
• Preparation of Thiosugars and Their Use
  申请人：Davis Benjamin Guy

  公开号：US20090176970A1

  公开（公告）日：2009-07-09

  A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

  一种制备由糖硫代糖（Saccharide-S-H）表示的硫代糖的方法，其中糖代表至少4个糖单元，包括将具有以下结构的相应化合物（P）糖硫代糖（P）进行桦还原：（P）糖硫代糖（P），其中（P）代表一个或多个O-或S-保护基。
• Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of <i>Leishmania major</i> infection
  作者：Chelsea L Rintelmann、Tara Grinnage-Pulley、Kathleen Ross、Daniel E K Kabotso、Angela Toepp、Anne Cowell、Christine Petersen、Balaji Narasimhan、Nicola Pohl

  DOI：10.3762/bjoc.15.58

  日期：——

  Leishmaniasis, a neglected tropical disease, currently infects approximately 12 million people worldwide with 1 to 2 million new cases each year in predominately underdeveloped countries. The treatment of the disease is severely underdeveloped due to the ability of the Leishmania pathogen to evade and abate immune responses. In an effort to develop anti-leishmaniasis vaccines and adjuvants, novel carbohydrate-based probes were made to study the mechanisms of immune modulation. In this study, a new bioerodible polyanhydride microparticle was designed and conjugated with a glycodendrimer molecular probe. This molecular probe incorporates a pathogen-like multivalent display of α-1,2-trimannose, for which a more efficient synthesis was designed, with a tethered fluorophore. Further attachment of the glycodendrimer to a biocompatible, surface eroding microparticle allows for targeted uptake and internalization of the pathogen-associated oligosaccharide by phagocytic immune cells. The α-1,2-trimannose-linked bioerodible microparticles were found to be safe after administration into the footpad of mice and demonstrated a similar response to α-1,2-trimannose-coated latex beads during L. major footpad infection. Furthermore, the bioerodible microparticles allowed for investigation of the role of pathogen-associated oligosaccharides for recognition by pathogen-recognition receptors during L. major-induced leishmaniasis.

  利什曼病是一种被忽视的热带疾病，目前全球大约有1200万人感染，每年有大约100万到200万新病例，主要发生在发展中国家。由于利什曼原虫能够逃避和减弱免疫反应，治疗这种疾病的方法严重不足。为了开发抗利什曼病的疫苗和佐剂，人们制作了基于碳水化合物的新的分子探针来研究免疫调节的机制。在这项研究中，设计了一种新的生物可降解的多酸酐微粒，并将其与一种糖基树状分子探针结合。这个分子探针结合了一种类似病原体的多价α-1,2-三甘露糖展示，为了更有效的合成，它还连接了一个荧光团。将糖基树状分子进一步附着在生物相容性、表面侵蚀的微粒上，允许吞噬免疫细胞针对性地摄取和内化与病原体相关的低聚糖。α-1,2-三甘露糖连接的生物可降解微粒在小鼠脚垫内注射后被认为是安全的，并且在利什曼原虫脚垫感染期间，对α-1,2-三甘露糖包被的乳胶珠的反应相似。此外，生物可降解微粒允许研究病原体相关低聚糖在利什曼原虫诱导的利什曼病期间被病原体识别受体的识别作用。
• Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2‐Aryl‐1,3‐dithiane 1‐Oxide ^†
  作者：Lei Cai、Jing Zeng、Ting Li、Ying Xiao、Xiang Ma、Xiong Xiao、Qin Zhang、Lingkui Meng、Qian Wan

  DOI：10.1002/cjoc.201900419

  日期：2020.1

  center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3‐diol protection. Most

  利用三氟甲磺酸酐（Tf 2O）。通过将高亲硫性启动子系统的高效性与脱水糖基化的逐步效率相结合，该试剂通过C1-半乙缩醛供体进行了分子间的氧代硫代缩醛化反应，以安装一个临时的离去基团，从而使远程位置的瞬变亲电子中心变为异头位置。拴在末端的三氟甲磺酸亚砜在分子内同时活化了硫化物，提供了碳碳鎓离子，从而促进了标题糖基化。除了可容纳广泛的官能团和不活跃的半缩醛底物外，目前的激活方案还证明了对1,3-二醇的保护是合宜的。最重要的是，该方法进一步为将硫化学应用于碳水化合物化学提供了新的视角。