(Z)-N-(5-deoxy-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide | 162920-12-9

• 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-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide
• 英文别名: (Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-1,4-furanose-5-ylidene)benzylamine N-oxide；1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-N-benzylmethanimine oxide
• CAS: 162920-12-9；191997-35-0
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: GOCQVECKTSSMNH-CGLOGNSJSA-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-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide 在 吡啶 、 氯化二乙基铝 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 5-(acetoxyamino)-N-benzyl-5-deoxy-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449
• 作为产物：
  描述：

  苯甲醛肟 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (Z)-N-(5-deoxy-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide
  参考文献：
  名称：

  以手性醛为束缚催化剂的烯丙胺的高度对映选择性分子间胺化反应

  摘要：

  手性醛：手性醛是对映选择性分子间加氢胺化的有效束缚催化剂，可提供高产率和优异对映选择性的邻位二胺基序（参见方案）。这项工作强调了简单的手性α-氧化醛作为有效的有机催化剂，能够通过瞬态分子内有效诱导不对称性。

  DOI：

  10.1002/chem.201203462

文献信息

• 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.
• Kolarovic; Fisera; Toma, Polish Journal of Chemistry, 2007, vol. 81, # 11, p. 1963 - 1970
  作者：Kolarovic、Fisera、Toma、Pronayova、Koos

  DOI：——

  日期：——
• 1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines
  作者：Pedro Merino、Santiago Franco、Francisco L. Merchan、Pilar Romero、Tomas Tejero、Santiago Uriel

  DOI：10.1016/j.tetasy.2003.08.027

  日期：2003.11

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.