2-naphthyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside | 1119240-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
• 英文别名: 2-naphthalenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；[(2R,3S,6R)-3-acetyloxy-6-naphthalen-2-yloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1119240-82-2
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: KPYFANYAZMUETB-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-萘酚 、 乙酰化葡萄烯糖 在 磷酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以82%的产率得到2-naphthyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
  参考文献：
  名称：

  A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst

  摘要：

  A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of alpha-selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.103

文献信息

• Gd(OTf) 3 catalyzed preparation of 2,3-unsaturated O -, S -, N -, and C -pyranosides from glycals by Ferrier Rearrangement
  作者：Peiran Chen、Jie Su

  DOI：10.1016/j.tet.2015.11.002

  日期：2016.1

  By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.

  通过使用Gd（OTf）3作为催化剂，已经通过Ferrier重排进行了2，3-不饱和糖苷的合成。一系列的2,3-不饱和ø - ，小号- ，Ñ - ，和Ç从3,4,6-三获得-glycosides ö乙酰基d -glucal，3,4,6-三- ø -苄基- d -glucal，和3,4-二- ö乙酰基升以良好的收率和高的选择性异头温和反应条件下-rhamnal。
• 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。
• Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals
  作者：Peiran Chen、Dalin Zhang

  DOI：10.1016/j.tet.2014.09.060

  日期：2014.11

  By using Sm(OTf)(3) as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-L-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-L-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. (C) 2014 Elsevier Ltd. All rights reserved.