4-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 14675-51-5

• 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: 4-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；-4,6-di-O-acetyl-2,3-didehydro-2,3-didesoxy-α-D-erythro-hexosid；p-Nitrophenyl-4,6-di-O-acetyl-2,3-didehydro-2,3-didesoxy-α-D-erythro-hexosid；(p-Nitro-phenyl)-4,6-di-O-acetyl-2,3-didehydro-2,3-didesoxy-α-D-erythro-hexosid；[(2R,3S,6R)-3-acetyloxy-6-(4-nitrophenoxy)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 14675-51-5
• 化学式: C₁₆H₁₇NO₈
• 分子量: 351.313
• InChiKey: SKOXNBYDOZPRJH-XHSDSOJGSA-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：

  4-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 palladium diacetate 咪唑 、 sodium methylate 、 四丁基硫酸氢铵 、 sodium hydride 、 三乙胺 、 氯乙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 106.0h， 生成 1,2,3,4-tetradeoxy-2',3',4',5'-tetrahydro-6-O-(tert-butyldimethylsilyl)-4'-methylene-D-lyxo-hex-1-enopyranoso-[4,3-b]furan
  参考文献：
  名称：

  Palladium-Mediated Cyclization on Carbohydrate Templates. 3. Extension of The Cyclization to the Threo Series.

  摘要：

  The palladium(0)-catalyzed Heck-type cyclization-beta-alkoxy elimination reaction leading to enantiopure bicyclic compounds in the case of erythro 2,3-unsaturated glycosides has been successfully extended to the three stereoisomer by only changing the aglycon moiety from an ethoxy group to an aryloxy moiety.

  DOI：

  10.1080/07328300008544075
• 作为产物：
  描述：

  对硝基苯酚 、 乙酰化葡萄烯糖 在 zinc dibromide 作用下， 以 氯仿 为溶剂， 反应 0.75h， 以57%的产率得到4-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  ZnBr₂-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols

  摘要：

  DOI：

  10.1080/00397911.2014.909490

文献信息

• Yadav; Reddy; Murthy, Synlett, 2000, # 10, p. 1450 - 1451
  作者：Yadav、Reddy、Murthy、Kumar

  DOI：——

  日期：——
• O- and N-Glycosidation of d-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis
  作者：Kyosuke Michigami、Masahiko Hayashi

  DOI：10.1016/j.tet.2011.11.084

  日期：2012.1

  We have disclosed the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity. The reaction would take place via allyloxycarbenium ion. (C) 2011 Elsevier Ltd. All rights reserved.
• Reaction of 2,3-unsaturated aryl glycosides with Lewis acids : a convenient entry to C-aryl glycosides
  作者：N.G. Ramesh、K.K. Balasubramanian

  DOI：10.1016/s0040-4039(00)79600-6

  日期：1992.5

  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.
• An Easy and Efficient Preparation of Aryl α-<i>O</i>-Δ²−Glycosides
  作者：I. Frappa、D. Sinou

  DOI：10.1080/00397919508011424

  日期：1995.10

  Ferrier reaction between acetylglycals and p-NO2, m-NO2 and p-t-butylphenol after recrystallization gave aryl O-Delta(2)-glycosides as the pure a anomers. Deacetylation of these compounds and benzylation of the crude diol led to the corresponding aryl alpha-O-Delta(2)-4,6-di-O-benzylglycosides in large amounts.