(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-stearamidoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1013637-70-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-stearamidoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: 1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-octadecenoyl-2-amino-ethanol；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(octadecanoylamino)ethoxy]oxan-2-yl]methyl acetate
• CAS: 1013637-70-1
• 化学式: C₃₄H₅₉NO₁₁
• 分子量: 657.843
• InChiKey: DZUPLVDYFDQBKF-SSWJQGRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  46
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  [(3aR,5R,6S,7S,7aR)-6,7-diacetyloxy-2-methyl-2-[2-(octadecanoylamino)ethoxy]-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以186 mg的产率得到(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-stearamidoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides

  摘要：

  β-半乳糖苷神经酰胺通过将非活性糖苷供体与锡醚反应获得了优异的产率和立体选择性。证明了锡醚与各种离去基–促进剂配对的广泛相容性。

  DOI：

  10.1039/b809570a

文献信息

• Glycosylation of Stannyl Ceramides Promoted by Modified Montmorillonite­ in Supercritical Carbon Dioxide
  作者：José Morales-Serna、Bao Nguyen、Eréndira García-Ríos、Rubén Gaviño、Jorge Cárdenas、Gustavo García de la Mora

  DOI：10.1055/s-0036-1591515

  日期：2018.2

  Abstract The direct glycosylation of ceramides in supercritical carbon dioxide (scCO2) successfully proceeded to produce β-glycolipids in high yield and with full stereoselectivity. The reaction is promoted by montmorillonite modified with a superacid (CF3SO3H). The value of this protocol was demonstrated in the efficient synthesis of isoglobotrihexosylceramide (iGB3). The direct glycosylation of ceramides

  摘要 神经酰胺在超临界二氧化碳（scCO 2）中的直接糖基化成功地以高收率和完全的立体选择性进行生产β-糖脂。该反应通过用超强酸（CF 3 SO 3 H）改性的蒙脱石来促进。该协议的价值在异源三异己糖基神经酰胺（iGB3）的有效合成中得到了证明。 神经酰胺在超临界二氧化碳（scCO 2）中的直接糖基化成功地以高收率和完全的立体选择性进行生产β-糖脂。该反应通过用超强酸（CF 3 SO 3 H）改性的蒙脱石来促进。该协议的价值在异源三异己糖基神经酰胺（iGB3）的有效合成中得到了证明。
• Highly efficient and stereoselective synthesis of β-glycolipids
  作者：José Antonio Morales-Serna、Omar Boutureira、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1039/b718521a

  日期：——

  beta-Galactosylceramide and glycolipid analogues were prepared in high yield and with complete chemo and stereoselectivity by reaction of alpha-iodo glycosides with stannyl ceramides, formed in situ. TBAI was used to activate both the iodogalactose and the stannyl ether.

  β-半乳糖基神经酰胺和糖脂类似物的制备是高产率的，并且通过α-碘糖苷与原位形成的苯乙烯基神经酰胺的反应具有完全的化学和立体选择性。TBAI被用来激活碘代半乳糖和甲锡醚。
• Efficient Synthesis of β-Glycosphingolipids by Reaction of Stannylceramides with Glycosyl Iodides Promoted by TBAI/AW 300 Molecular Sieves
  作者：José Antonio Morales-Serna、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1002/ejoc.200900424

  日期：2009.8

  TBAI and acid-washed molecular sieves efficiently promoted the glycosylation of stannylceramides with glycosyl iodides. This direct glycosylation reaction reduces the overall number of synthetic steps and provides rapid access to β-glycosphingolipids such as GalCer, β-lactosylceramide, and iGB3 in good yield and with complete chemo- and stereoselectivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  TBAI 和酸洗的分子筛有效地促进了甲磺酸基神经酰胺与糖基碘的糖基化。这种直接糖基化反应减少了合成步骤的总数，并以良好的收率和完全的化学和立体选择性快速获得了 β- 鞘糖脂，例如 GalCer、β-乳糖苷神经酰胺和 iGB3。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)。