N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine | 22435-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine
• 英文别名: N-Ethoxycarbonylvinyl-L-rhamnopyranosylamine；N-(2,2-Bis-aethoxycarbonyl-vinyl)-β-L-rhamnopyranosylamin；diethyl 2-[[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]amino]methylidene]propanedioate
• CAS: 22435-67-2
• 化学式: C₁₄H₂₃NO₈
• 分子量: 333.339
• InChiKey: ZTEVGXLVZFJIBX-CFVLRQLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine 在 吡啶 、 sodium methylate 、 对甲苯磺酸 、 乙硫醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、2.67 kPa 条件下， 反应 77.25h， 生成 1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-β-L-rhamnopyranosylamine
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003

文献信息

• Ring contraction of glycopyranosyl enamines: an easy route to furanoid thioglycosides of 5-aminosugars
  作者：M.Ángeles Pradera、Francisco J. Sayago、José M. Illangua、Manuel Angulo、Consolación Gasch、José Fuentes

  DOI：10.1016/j.tetasy.2004.05.027

  日期：2004.7

  The reaction of glycohexapyranosyl enamines, having 2- and 3-hydroxyl groups in a cis-relationship with 12-dimethoxypropane, induces ring contraction of the sugar ring with formation of 2,3-O-isopropylidene furanoid glycosylenamines. 5-O-Mesylation of these compounds. followed by formation of anhydroazasugars and nucleophilic ring opening, with thiols, produces alkyl and aryl thiofuranosides of 5-aminosugars. (C) 2004 Elsevier Ltd. All rights reserved.
• Tri-O-benzoyl-β-l-rhamnopyranosyl and β-l-fucopyranosyl isothiocyanates. Partially protected β-l-rhamnopyranosylenamines
  作者：José Fuentes-Mota、Eugenia López-Barba、Inmaculada Robina、José Molina Molina、Dolores Portal Olea

  DOI：10.1016/0008-6215(93)84250-a

  日期：1993.9

  Regioselective benzoylations of N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (1) yielded 2,3-di-O- (3), 3,4-di-O- (4), and 3-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (5) together with the tri-O-benzoylated derivative 2. Syntheses of 2,3,4-tri-O-benzoyl-beta-L-rhamno- (7) and -beta-L-fuco-pyranosyl isothiocyanate (13) from 2 and L-fucopyranosylamine, respectively, are described. N-Phenacyl-N'-(2,3,4-tri-O-benzoyl-beta-L-rhamno- (8) and -beta-L-fuco-pyranosylthiourea (14) were prepared from 7 and 13, respectively, by reaction with phenacylamine. Conformational properties and MS data of the prepared compounds are discussed.
• Fuentes, Jose; Gonzalez-Eulate, Enrique; Lopez-Barba, Eugenia, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 1, p. 79 - 94
  作者：Fuentes, Jose、Gonzalez-Eulate, Enrique、Lopez-Barba, Eugenia、Robina, Inmaculada

  DOI：——

  日期：——
• Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides
  作者：José Fuentes、Francisco J. Sayago、José M. Illangua、Consolación Gasch、Manuel Angulo、M. Ángeles Pradera

  DOI：10.1016/j.tetasy.2004.01.003

  日期：2004.2

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.