6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-arabino-hept-2-enono-1,4-lactone | 127997-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-arabino-hept-2-enono-1,4-lactone
• 英文别名: 3-Oxazolidinecarboxylic acid, 4-((2,5-dihydro-5-oxo-2-furanyl)hydroxymethyl)-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R-(4R*(R*(R*))))-；tert-butyl (4R)-4-[(R)-hydroxy-[(2R)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 127997-05-1
• 化学式: C₁₅H₂₃NO₆
• 分子量: 313.351
• InChiKey: XLXUOUVMYCUWGG-CKYFFXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-arabino-hept-2-enono-1,4-lactone 在 吡啶 、 4-二甲氨基吡啶 、 potassium permanganate 、 dicyclohexane-crown-6 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-tert-butyl 4-((S)-((2S,3S,4R)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)((trimethylsilyl)oxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives

  摘要：

  Two enantio couples of terminal C-glycopyranosyl-alpha-amino acids, namely the aminopyranuronic acids L-9, D-9 and L-10, D-10, have been synthesized from the serine-derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4. The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furanose-to-pyranose ring expansion to construct the sugar skeleton with the proper stereochemistry. In our best performance, homogeneous L-9 was prepared from L-2 in four steps and 10 reactions in 20% overall yield.

  DOI：

  10.1021/jo00023a015
• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 三氟化硼乙醚 作用下， 以86%的产率得到6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-arabino-hept-2-enono-1,4-lactone
  参考文献：
  名称：

  Highly stereocontrolled total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives

  摘要：

  通过丁烯内酯中间体D-2和L-2，对两种新型α-氨基糖苷酸（对映体对D-10和L-10）进行了选择性合成。

  DOI：

  10.1039/c39910000603

文献信息

• The four-carbon elongation of three-carbon chiral synthons using 2-(trimethylsiloxy)furan: highly stereocontrolled entry to enantiomerically pure seven-carbon α,β-unsaturated 2,3-dideoxy-aldonolactones
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu、Giovanna Gasparri Fava、Marisa Ferrari Belicchi

  DOI：10.1016/s0040-4020(01)87777-2

  日期：1990.1
• Synthesis of enantiomerically pure 2,3-dideoxy-hept-2-enono-1,4-lactone derivatives diastereoselective addition of 2-(trimethylsiloxy)furan to -glyceraldehyde and -serinal-based three-carbon synthons
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu

  DOI：10.1016/s0040-4039(01)93777-3

  日期：1989.1
• CASIRAGHI, GIOVANNI;COLOMBO, LINO;RASSU, GLORIA;SPANUA, PIETRO, TETRAHEDRON LETT., 30,(1989) N9, C. 5325-5328
  作者：CASIRAGHI, GIOVANNI、COLOMBO, LINO、RASSU, GLORIA、SPANUA, PIETRO

  DOI：——

  日期：——
• Total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu

  DOI：10.1021/jo00023a015

  日期：1991.11

  Two enantio couples of terminal C-glycopyranosyl-alpha-amino acids, namely the aminopyranuronic acids L-9, D-9 and L-10, D-10, have been synthesized from the serine-derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4. The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furanose-to-pyranose ring expansion to construct the sugar skeleton with the proper stereochemistry. In our best performance, homogeneous L-9 was prepared from L-2 in four steps and 10 reactions in 20% overall yield.
• Highly stereocontrolled total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu

  DOI：10.1039/c39910000603

  日期：——

  An extremely selective synthesis of two novel α-aminouronic acids, the enantio-pair D-10 and L-10, through the butenolide intermediates D-2 and L-2 is described.

  通过丁烯内酯中间体D-2和L-2，对两种新型α-氨基糖苷酸（对映体对D-10和L-10）进行了选择性合成。