methyl 4,6-di-O-benzyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside | 63479-65-2

• 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: methyl 4,6-di-O-benzyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6S)-6-methoxy-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 63479-65-2
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: CXWCUONVIPTJTJ-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,6-di-O-benzyl glucal 在 gold(III) chloride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 methyl 4,6-di-O-benzyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3

  摘要：

  The stereoselective synthesis of 2,3-unsaturated alpha-D-glucosides by the S(N)2' addition of diverse aglycones onto 4,6-di-O-benzyl-3-O-propargyl glucal was achieved using a catalytic quantity of AuCl3. The Au catalyzed reaction was explored using various aliphatic, aromatic, alicyclic and monosaccharide aglycones. The current protocol tolerates diverse functional groups and is highly stereoselective, fast, catalytic and mild. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.048

文献信息

• FeCl₃/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-<i>O</i>-Benzyl-D-glucal
  作者：Yuling Mei、Youxian Dong、Juan Li、Bo Zhang、Guosheng Sun、Jiafen Zhou、Wenshuai Si、Yiwen Han、Zhenliang Wu、Jianbo Zhang

  DOI：10.1080/07328303.2020.1788575

  日期：2020.7.23

  Abstract FeCl3/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-D-glucal, which is a relatively unreactive substrate for this type of reaction. The method was applicable to a wide range of alcohols, especially phenols. A series of 2,3-unsaturated-O-glucosides were prepared efficiently (47–92%) by this method under mild conditions

  摘要FeCl3 / C被用作通过3,4,6-tri-O-苄基-D-葡糖的Ferrier型重排进行糖基化的有效且方便的启动子，它是此类反应的相对反应性底物。该方法适用于多种醇，尤其是酚。通过该方法在温和的条件下，可以有效地制备一系列2，3-不饱和的O-葡萄糖苷（47-92％）。
• Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride
  作者：Paramathevar Nagaraj、Namakkal G. Ramesh

  DOI：10.1016/j.tetlet.2009.04.084

  日期：2009.7

  Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature. This methodology obviates the need for protecting and/or activating the C-3 hydroxyl group of glycals. The reaction works in equal ease with both

  已经证明无水InCl 3通过在糖基的C -3位置上的羟基的直接烯丙基取代有效地催化费列重排，从而在环境温度下以高收率提供相应的2，3-不饱和糖苷。该方法避免了保护和/或活化糖基的C -3羟基的需要。将反应工作在同样容易与两个4,6-二ö苄基d -glucal和4,6-二- ö苄基d -galactal。InCl 3的温和性使该方法与具有酸不稳定基团的糖基受体兼容。反应的普遍性已通过多种醇，酚和糖亲核试剂得到证明。
• Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols
  作者：D. Bradley G. Williams、Sandile B. Simelane、Henok H. Kinfe

  DOI：10.1039/c2ob25540e

  日期：——

  A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

  提出了在Al（OTf）3催化的醇直接添加或某些糖基中的Ferrier重排反应之间的温度控制机制切换。研究了范围和局限性以及糖基上保护基的立体化学和性质的影响。
• NaHSO4 supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals
  作者：Henok H. Kinfe、Fanuel M. Mebrahtu、Khuphukile Sithole

  DOI：10.1016/j.carres.2011.08.023

  日期：2011.11

  NaHSO(4) supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-D-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.

  载于硅胶上的NaHSO（4）催化3,4,6-tri-O-乙酰基-D-葡萄糖与醇和硫醇的Ferrier重排反应，得到相应的2,3-不饱和糖苷，其端基异构体选择性高，且对反应时间短，产率极高。
• Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation
  作者：Guisheng Zhang、Qingfeng Liu、Lei Shi、Jiuxia Wang

  DOI：10.1016/j.tet.2007.10.097

  日期：2008.1

  O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glycosides via Ferrier rearrangement. The reaction of the perbenzyl glucal with various alcohols catalyzed by ferric sulfate hydrate (Fe2(SO4)3·xH2O) was successfully carried out to give 2,3-unsaturated d-O-glucosides with exclusive α-selectivity and

  我们已经开发了一种新颖的基于糖基的O-糖基化反应，其中底物不仅是过乙酰基糖基，而且是过苄基葡糖基，以通过Ferrier重排提供相应的2,3-不饱和-O-糖苷。成功地进行了苄基葡糖醛与水合硫酸铁（Fe 2（SO 4）3 · x H 2 O）催化的各种醇的反应，得到2,3-不饱和d- O-葡萄糖苷，具有独特的α-选择性和没有观察到加成产物2-脱氧己吡喃糖苷的形成。这是关于全烷基糖有效经历费勒重排而不是由路易斯酸催化的醇加成的首次报道。铁2（SO 4）3 · x H 2 O是一种有效，方便且对环境无害的多相催化剂。它具有较低的催化负荷，可回收利用，且活性没有明显降低。