7-acetamido-8,9,11-tri-O-acetyl-6,10-anhydro-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gluco-undecitol | 443916-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-acetamido-8,9,11-tri-O-acetyl-6,10-anhydro-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gluco-undecitol
• 英文别名: tert-butyl (4S)-4-[3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 443916-59-4
• 化学式: C₂₇H₄₄N₂O₁₁
• 分子量: 572.653
• InChiKey: ZFMPFNKFPYBYNS-ZJCHSKCTSA-N

物化性质

• 沸点：
  662.3±55.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  7-acetamido-8,9,11-tri-O-acetyl-6,10-anhydro-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gluco-undecitol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 6,10-anhydro-7-acetamido-8,9,11-tri-O-acetyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-gluco-undeconic acid
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m
• 作为产物：
  描述：

  (R)-4-[3-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 吡啶 、 4-二甲氨基吡啶 、 palladium dihydroxide 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~85.0 ℃ 、700.01 kPa 条件下， 反应 14.0h， 生成 7-acetamido-8,9,11-tri-O-acetyl-6,10-anhydro-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gluco-undecitol
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m