{(S)-1-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester | 1054651-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(S)-1-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-[(3aR,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-oxoethyl]carbamate
• CAS: 1054651-06-7
• 化学式: C₁₉H₃₁NO₈
• 分子量: 401.457
• InChiKey: GQYNOGXZQNJVFJ-KYFQHEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 吡啶 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (S)-tert-Butoxycarbonylamino-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid methyl 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：

  C-{(S)-C-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-C-thiazol-2-yl}-methylamine 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 {(S)-1-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-oxo-ethyl}-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

文献信息

• 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).