N-Benzyl-N-[(R)-thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-hydroxylamine | 191997-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Benzyl-N-[(R)-thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-hydroxylamine
• 英文别名: N-benzyl-N-[(R)-1,3-thiazol-2-yl-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]hydroxylamine
• CAS: 191997-85-0
• 化学式: C₄₅H₄₆N₂O₆S
• 分子量: 742.936
• InChiKey: WVLKNOLRIDCMOV-CNGYLHDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-[(R)-thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-hydroxylamine 在 titanium(III) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 12.25h， 生成 [(R)-Thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines

  摘要：

  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).

  DOI：

  10.1021/jo970290a
• 作为产物：
  描述：

  2-lithiothiazole 、 N-benzyl-1-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methanimine oxide 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 N-Benzyl-N-[(S)-thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-hydroxylamine 、 N-Benzyl-N-[(R)-thiazol-2-yl-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-hydroxylamine
  参考文献：
  名称：

  Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines

  摘要：

  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).

  DOI：

  10.1021/jo970290a

文献信息

• Determination of the absolute configuration of α-amino-2-alkylthiazoles by circular dichroism
  作者：Francisco L. Merchán、Pedro Merino、Isabel Rojo、Tomás Tejero、Alessandro Dondoni

  DOI：10.1016/0957-4166(95)00286-x

  日期：1995.9

  Correlation between absolute configuration at the alpha-centre of the thiazole ring in the title compounds and the sign of their Cotton effect (CE) in the range 217-230 nm is reported.