(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(but-3-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1174137-50-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(but-3-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: 3-butenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；butenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS: 1174137-50-8
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: YHPGWRDWGNCPRH-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(but-3-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 安息香双甲醚 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Development of Mannosylated Lipid Nanoparticles for mRNA Cancer Vaccine with High Antigen Presentation Efficiency and Immunomodulatory Capability

  摘要：

  Insufficient accumulation of lipid nanoparticles (LNPs)‐based mRNA vaccines in antigen presenting cells remains a key barrier to eliciting potent antitumor immune responses. Herein, we develop dendritic cells (DCs) targeting LNPs by taking advantage of mannose receptor‐mediated endocytosis. Efficient delivery of mRNA to DCs is achieved in vitro and in vivo utilizing the sweet LNPs (STLNPs‐Man). Intramuscular injection of mRNA vaccine (STLNPs‐Man@mRNAOVA) results in a four‐fold higher uptake by DCs in comparison with commercially used LNPs. Benefiting from its DCs targeting ability, STLNPs‐Man@mRNAOVA significantly promotes the antitumor performances, showing a comparable therapeutic efficacy by using one‐fifth of the injection dosage as the vaccine prepared from normal LNPs, thus remarkably avoiding the side effects brought by conventional mRNA vaccines. More intriguingly, STLNPs‐Man@mRNAOVA exhibits the ability to downregulate the expression of cytotoxic T‐lymphocyte‐associated protein 4 on T cells due to the blockade of CD206/CD45 axis, showing brilliant potentials in promoting antitumor efficacy combined with immune checkpoint blockade therapy.

  DOI：

  10.1002/anie.202318515
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(but-3-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Cross Metathesis Assisted Solid-Phase Synthesis of Glycopeptoids

  摘要：

  A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yields. This systematic solid-phase CM study can provide facile access to the molecular sources of glycopeptidomimetics and postchemical modifications on various molecular scaffolds.

  DOI：

  10.1021/ol300808c

文献信息

• Acid‐Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water
  作者：Brian J. J. Timmer、Olof Ramström

  DOI：10.1002/chem.201903155

  日期：2019.11.13

  The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized α-d-manno- and α-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis

  证明了在水性介质中的烯烃复分解反应中使用未保护的碳水化合物的能力。通过在弱酸性水溶液条件下使用水溶性，胺官能化的Hoveyda-Grubbs催化剂，可以通过最大限度地减少非生产性螯合和异构化来实现未保护的烯烃官能化的α-d-甘露聚糖和α-d-吡喃半乳糖苷的自易位。 。与烯丙醇的交叉复分解也可以以合理的选择性实现。少量（2.5体积％）的乙酸的存在增加了自易位产物的形成，同时显着减少了烯烃的异构化过程。此外，在大量（0.01 mm）蛋白质存在下，催化活性得以保留，强调了在生物条件下这种碳-碳键形成反应的潜力。这些结果证明了在与生物系统相容的温和条件下在烯烃复分解反应中直接使用未保护的碳水化合物结构的潜力，从而使其能够用于例如药物发现和蛋白质衍生化。
• Hryniewicka; Walejko; Morzycki, Polish Journal of Chemistry, 2009, vol. 83, # 1, p. 75 - 80
  作者：Hryniewicka、Walejko、Morzycki、Witkowski

  DOI：——

  日期：——