N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)methanesulfonamide | 471923-23-6

• 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: N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)methanesulfonamide
• 英文别名: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-4-methanesulfonamide；4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-N-methanesulfonamide；4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl methanesulfonamide；4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosylmethanesulfonamide
• CAS: 471923-23-6
• 化学式: C₁₁H₁₇NO₇S
• 分子量: 307.324
• InChiKey: COUYLHIVGSKSST-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  甲基磺酰胺 、 乙酰化葡萄烯糖 在 gadolinium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 以84%的产率得到N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)methanesulfonamide
  参考文献：
  名称：

  Gd（OTf）3通过Feer重排从糖类催化制备2,3-不饱和O-，S-，N-和C-吡喃糖苷

  摘要：

  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。

  DOI：

  10.1016/j.tet.2015.11.002

文献信息

• Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated <i>O</i>-, <i>C</i>-, <i>N</i>- and <i>S</i>-linked glycosides
  作者：Madhu Babu Tatina、Xia Mengxin、Rao Peilin、Zaher M A Judeh

  DOI：10.3762/bjoc.15.125

  日期：——

  A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic

  开发了一种方便的方案，用于使用20摩尔％的全氟苯基硼酸催化剂通过Ferrier重排合成2，3-不饱和C-，O-，N-和S-连接的糖苷（烯醇）。使用该方案，D-葡糖醛酸和L-鼠李糖醛与各种C-，O-，N-和S-亲核试剂反应，以高达98％的收率（主要是α-异头异构体选择性）提供各种糖苷。全氟苯基硼酸在非常温和的反应条件下成功催化了多种底物（葡糖醛和亲核试剂）。
• A mild and efficient synthetic protocol for Ferrier azaglycosylation promoted by ZnCl2/Al2O3
  作者：Feiqing Ding、Ronny William、Bala Kishan Gorityala、Jimei Ma、Siming Wang、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.04.045

  日期：2010.6

  An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with good yields and preferential alpha-anomeric selectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• An eco-friendly tandem tosylation/Ferrier N -glycosylation of amines catalyzed by Er(OTf) 3 in 2-MeTHF
  作者：Monica Nardi、Natividad Herrera Cano、Antonio De Nino、Maria Luisa Di Gioia、Loredana Maiuolo、Manuela Oliverio、Ana Santiago、Diletta Sorrentino、Antonio Procopio

  DOI：10.1016/j.tetlet.2017.03.047

  日期：2017.5

  Er(OTf)(3) in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-d-glucal and different nucleophiles affording good results in a short time. (C) 2017 Published by Elsevier Ltd.
• Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation
  作者：Thurpu Raghavender Reddy、Sravanthi Chittela、Sudhir Kashyap

  DOI：10.1016/j.tet.2014.10.024

  日期：2014.12

  An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or 'N-pseudoglycals' in good yields (64-98%). High alpha-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Zn(II) Triflate-Catalyzed<i>N</i>-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides
  作者：Thurpu Raghavender Reddy、Suresh Kumar Battina、Sudhir Kashyap

  DOI：10.1080/07328303.2015.1018994

  日期：2015.3.24

  GRAPHICAL ABSTRACT[GRAPHICS]A highly efficient and mild method for the synthesis of glycosyl sulfonamides and glycosyl amides from glycal has been described using Zn(OTf)(2) as an economical and environmentally friendly catalyst. Various N-nucleophiles comprising sulfonamides, benzamides, and carbamates were glycosylated with glycals to obtain corresponding 2,3-unsaturated N-glycosides in good yields.