L-menthyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1629041-66-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: L-menthyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• 英文别名: L-menthyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
• CAS: 1629041-66-2
• 化学式: C₂₀H₃₂O₆
• 分子量: 368.47
• InChiKey: QPWNADCMIQNLGA-KMHZDYFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  L-薄荷醇 、 乙酰化葡萄烯糖 在 gold(III) chloride 、 苯乙炔 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以83.333%的产率得到
  参考文献：
  名称：

  氯化金 (III) 和苯乙炔：一种用于费里尔重排的催化剂系统，以及作为糖基供体的 1-O-乙酰糖的 O-糖基化

  摘要：

  我们开发了一种新的催化剂体系，包含 AuCl3 和苯乙炔，可促进具有不同亲核试剂的糖类和 2-乙酰氧基甲基糖类的费里尔重排，以及 1-O-乙酰糖的 O-糖基化，以通过以下方式在室温下获得各种有用的糖苷中继催化。对于 Ferrier 重排观察到良好的异头异构体选择性，而 1-O-乙酰糖的 O-糖基化产生具有中等至极好选择性的非对映异构体混合物。

  DOI：

  10.1002/ejoc.201402606

文献信息

• Copper(<scp>ii</scp>)-catalyzed stereoselective 1,2-addition <i>vs</i>. Ferrier glycosylation of “armed” and “disarmed” glycal donors
  作者：Manoj Kumar、Thurpu Raghavender Reddy、Aakanksha Gurawa、Sudhir Kashyap

  DOI：10.1039/d0ob01042a

  日期：——

  Selective activation of “armed’ and ‘'disarmed” glycal donors enabling the stereo-controlled glycosylations by employing Cu(II)-catalyst as the promoter has been realized. The distinctive stereochemical outcome in the process is mainly influenced by the presence of diverse protecting groups on the donor and the solvent system employed. The protocol is compatible with a variety of aglycones including

  通过使用Cu（II）-催化剂作为启动子，实现了“武装”和“解除武装”的糖基供体的选择性激活，从而实现了立体控制的糖基化。在该方法中独特的立体化学结果主要受供体和所用溶剂体系上存在各种保护基的影响。该方案可与多种糖苷配基（包括碳水化合物，氨基酸和天然产物）兼容，以高α-异头异构体选择性获得脱氧糖苷和糖缀合物。值得注意的是，该方法的合成实用性已被充分验证用于包含2-脱氧成分的三糖的立体选择性组装。涉及氘代实验的机理研究验证了合成-在武装供体的双键上进行非对映体选择性的1,2-加成受体。
• Copper(II) Triflate as a Mild and Efficient Catalyst for Ferrier Glycosylation: Synthesis of 2,3-Unsaturated O-Glycosides
  作者：Palakodety Radha Krishna、Sudhir Kashyap、Batthula Srinivas、Thurpu Reddy

  DOI：10.1055/s-0033-1341232

  日期：——

  Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)(2) as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.
• Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
  作者：Peiran Chen、Shan Li

  DOI：10.1016/j.tetlet.2014.08.092

  日期：2014.10

  By using Y(OTf)(3) as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal, and 3,4,6-tri-O-benzyl-D-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-D-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon. (C) 2014 Elsevier Ltd. All rights reserved.