p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside | 98392-78-0

• 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: p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside
• 英文别名: p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythrohex-2-enopyranoside；[(2R,3S)-3-acetyloxy-6-(4-nitrophenoxy)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 98392-78-0
• 化学式: C₁₆H₁₇NO₈
• 分子量: 351.313
• InChiKey: SKOXNBYDOZPRJH-QMRHZFGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside 在 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以30%的产率得到Acetic acid (2R,3S)-2-acetoxymethyl-6-(2-hydroxy-5-nitro-phenyl)-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Reaction of 2,3-unsaturated aryl glycosides with Lewis acids : a convenient entry to C-aryl glycosides

  摘要：

  A facile synthesis of 2',3'-unsaturated-C-aryl glycosides by BF3.Et2O mediated 'O' to 'C' transformation of 2,3-unsaturated aryl glycosides is reported.

  DOI：

  10.1016/s0040-4039(00)79600-6
• 作为产物：
  描述：

  对硝基苯酚 、 乙酰化葡萄烯糖 在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 、 dysprosium(III) trifluoromethanesulfonate 作用下， 反应 2.0h， 以85%的产率得到p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Dy（OTf）3-固定在离子液体中：一种新颖的可循环使用的反应介质，用于合成2,3-不饱和糖吡喃糖苷

  摘要：

  D-乙二醇与多种酒类， 酚类 和羟基α-氨基酸在5 mol％的存在下 f酸f 固定在 1-丁基-3-甲基咪唑鎓六氟磷酸盐在温和的反应条件下，以高产率和高α-选择性得到相应的2，3-不饱和糖吡喃糖苷。这催化剂 固定在 离子液体 在随后的反应中将其再循环，没有任何明显的活性损失。

  DOI：

  10.1039/b206957c

文献信息

• An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement
  作者：N. Raghavendra Swamy、Y. Venkateswarlu

  DOI：10.1055/s-2002-23551

  日期：——

  The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.

  已经证明三-O-乙酰基-D-葡糖醛和三-O-苄基-D-葡糖醛与各种醇和硫醇反应，在环境温度下通过乙腈中的三氯化铋以优异的产率提供相应的吡喃糖苷。
• A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides
  作者：Antonio Procopio、Renato Dalpozzo、Antonio De Nino、Loredana Maiuolo、Monica Nardi、Manuela Oliverio、Beatrice Russo

  DOI：10.1016/j.carres.2007.05.034

  日期：2007.10

  Er(OTf3 is a useful catalyst for the Ferrier rearrangement furnishing high yields of O- and S-glycosides. The transforination has wide applicability, cleaner reaction profiles, mild reaction conditions, and high stereoselectivity and the catalyst, which is also commercially available, can be recovered and reused. (c) 2007 Elsevier Ltd. All rights reserved.
• Mild and Highly Efficient Stereoselective Synthesis of 2,3‐Unsaturated Glycopyranosides using La(NO₃)₃ · 6H₂O as a Catalyst: Ferrier Rearrangement
  作者：N. Suryakiran、S. Malla Reddy、M. Srinivasulu、Y. Venkateswarlu

  DOI：10.1080/00397910701744170

  日期：2008.1

  A mild and highly efficient stereoselective reaction of 3,4,6-tri-O-acetyl-D-glucal with a variety of nucleophiles, viz. alcohols, phenols, thiols, thiophenols, and allyl trimethyl silane (TMS), in the presence of 5 mol% of lanthanum(III) nitrate hexahydrate under solvent-free conditions yielded the corresponding 2,3-unsaturated glycopyranosides (pseudoglycals) in excellent yields.
• Microwave Induced Ferrier Rearrangement
  作者：S. Sowmya、K. K. Balasubramanian

  DOI：10.1080/00397919408010221

  日期：1994.8

  A short and facile entry to the 2, 3-unsaturated O-arylglyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
• Synthesis of 2,3-unsaturated glycosides via metal-free Ferrier reaction
  作者：Kavita De、Julien Legros、Benoit Crousse、Danièle Bonnet-Delpon

  DOI：10.1016/j.tet.2008.09.005

  日期：2008.11

  Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of 2,3-unsaturated glycosides through allylic rearrangement of 3,4,6-tri-O-acetyl glucal. This metal-free, exclusively solvent-promoted Ferrier glycosylation, affords products in good to excellent yields and with good a-selectivity. (c) 2008 Elsevier Ltd. All rights reserved.