(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide | 161614-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide
• 英文别名: 1-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-N-benzylmethanimine oxide
• CAS: 161614-79-5；191997-34-9
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: GOCQVECKTSSMNH-ZHIAPSOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide 在 ruthenium trichloride 、 sodium periodate 、 titanium(III) chloride 、 氯化二乙基铝 、 silica gel 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 乙醚 、 正己烷 、 水 、 乙腈 为溶剂， 反应 26.33h， 生成 methyl (2S)-2-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(phenylmethoxycarbonylamino)acetate
  参考文献：
  名称：

  Applications of Sugar Nitrones in Synthesis:  The Total Synthesis of (+)-Polyoxin J¹

  摘要：

  A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and amination of sugar-derived aldehydes employing their nitrones as iminium derivatives and the furan ring as a masked carboxyl. Thus, the stereoselective addition of 2-lithiofuran to the L-threose derived N-benzyl nitrone 5 followed by reduction of the resulting hydroxylamine to amine, carbamoylation of the free hydroxy group, and oxidative cleavage of the furan ring to the carboxylate group gave a protected derivative of 3 (30%). The same method was followed for the synthesis of the ribofuranosyl alpha-amino acid nucleoside 4 (12.6%) starting from the D-ribose derived nitrone 6. The final coupling was performed by the N-hydroxysuccinimide active ester method in DMSO with the Hunig base (i-Pr2EtNH) using a derivative of 3 and unprotected 4.

  DOI：

  10.1021/jo9702913
• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 、 N-苄基羟胺 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide
  参考文献：
  名称：

  胸腺嘧啶多恶菌素C的全合成

  摘要：

  基于2-甲基硫代呋喃（一个掩蔽的羧酸酯基团）立体控制地添加到衍生自甲基2,3 - O-异亚丙基-二烯丙基-的N-苄基硝酮的6个步骤（总收率的7.2％）中的胸腺嘧啶多恶菌素C的快速合成描述了d-核呋喃糖苷。

  DOI：

  10.1016/s0040-4039(00)78564-9

文献信息

• Dondoni, Alessandro; Franco, Santiago; Junquera, Federico, Chemistry - A European Journal, 1995, vol. 1, # 8, p. 505 - 520
  作者：Dondoni, Alessandro、Franco, Santiago、Junquera, Federico、Merchan, Francisco L.、Merino, Pedro、et al.

  DOI：——

  日期：——
• Synthesis of N-Benzyl Nitrones
  作者：A. Dondoni、S. Franco、F. Junquera、F. L. Merchán、P. Merino、T. Tejero

  DOI：10.1080/00397919408010565

  日期：1994.10

  A general procedure for the synthesis of twenty-seven chiral and achiral N-benzyl nitrones 1 is described.
• Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines
  作者：Alessandro Dondoni、Federico Junquera、Francisco Luis Merchán、Pedro Merino、Marie-Christine Scherrmann、Tomas Tejero

  DOI：10.1021/jo970290a

  日期：1997.8.1

  A route to epimeric carbon-linked glycoglycines that exploits the stereoselective addition of 2-lithiofuran and 2-lithiothiazole to sugar nitrones has been described. The reaction occurs with opposite diastereofacial selectivity depending on whether the free nitrone or the diethyl aluminum chloride precomplexed derivative is employed. The resulting furyl or thiazolyl hydroxylamines are dehydroxylated to amines by the action of titanium(III) chloride. From these compounds the amino acids are revealed by the oxidative cleavage of the furan ring or by the conversion of the thiazole into the formyl group and oxidation to carboxylic acid. Compounds have been prepared wherein the alpha-amino acid moiety is installed at C-4 and C-1 of furanoses (ribo, manno, xylo, and lyxo) and at C-5 and C-1 of a pyranose (galacto).
• Porphyrins in 1,3-dipolar cycloaddition reactions with sugar nitrones. Synthesis of glycoconjugated isoxazolidine-fused chlorins and bacteriochlorins
  作者：Ana M.G Silva、Augusto C Tomé、Maria G.P.M.S Neves、Artur M.S Silva、José A.S Cavaleiro、Daniela Perrone、Alessandro Dondoni

  DOI：10.1016/s0040-4039(01)02243-2

  日期：2002.1

  Glycoconjugated isoxazolidine-fused chlorins and bacteriochlorins were prepared in moderate to good yields by 1,3-dipolar cycloaddition reactions of meso-tetrakis(pentafluorophenyl)porphyrin with glycosyl nitrones. (C) 2002 Elsevier Science Ltd. All rights reserved.