2,3,4-Tri-O-pivaloyl-α,β-arabinopyranose | 138892-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-Tri-O-pivaloyl-α,β-arabinopyranose
• 英文别名: 2,3,4-tri-O-pivaloyl-D-arabinopyranose；Tri-O-pivaloyl-D-arabinopyranose；pivaloyl-arabinopyranose；[(3R,4R,5S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-hydroxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 138892-03-2
• 化学式: C₂₀H₃₄O₈
• 分子量: 402.485
• InChiKey: CTDLTYCMOSZNDM-HABKJSAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl azide 在 镍 盐酸 、 水 、 氢气 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -25.0~25.0 ℃ 、101.33 kPa 条件下， 反应 89.0h， 生成 2,3,4-Tri-O-pivaloyl-α,β-arabinopyranose
  参考文献：
  名称：

  Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reaktions on Carbohydrate Templates

  摘要：

  L-氨基酸衍生物在斯特克反应和乌吉反应中采用2,3,4-三-O-庚酰基-α-D-阿拉伯吡喃糖胺或2,3,4-三-O-庚酰基-β-L-岩藻糖吡喃糖胺作为手性辅助剂，立体选择性合成，产率高。

  DOI：

  10.1055/s-1991-26641

文献信息

• Arabinosylamine in Asymmetric Syntheses of Chiral Piperidine Alkaloids
  作者：Horst Kunz、Birgit Kranke、Dominique Hebrault、Martin Schultz-Kukula

  DOI：10.1055/s-2004-817775

  日期：——

  The stereodifferentiating potential of arabinosyl aldimines was utilized in stereoselective syntheses of 2-substituted dehydropiperidinones and their further transformation to 2,6-cis-substituted piperidinones. The absolute configuration was proven by X-ray analysis and by the synthesis of the enantiomerically pure alkaloid (+)-dihydropinidine. The presented method offers the possibility to synthesize

  阿拉伯糖醛亚胺的立体分化潜力可用于立体选择性合成 2-取代脱氢哌啶酮及其向 2,6-顺式取代哌啶酮的进一步转化。通过 X 射线分析和对映体纯生物碱 (+)-二氢吡啶的合成证明了绝对构型。所提出的方法提供了合成哌啶衍生物对映异构体的可能性，这些衍生物是通过应用相应的半乳糖胺辅助剂获得的。
• Carbohydrates as Chiral Templates: Stereoselective Synthesis of (<i>R</i>)- and (<i>S</i>)-α-Aminophosphonic Acid Derivatives
  作者：Sabine Laschat、Horst Kunz

  DOI：10.1055/s-1992-34155

  日期：——

  The stereoselective synthesis of diethyl (S)- or (R)-α-[(O-pivaloyl-hexapyranosyl) amino]benzylphosphonates is achieved via Lewis acid catalyzed addition of diethyl phosphite to O-pivaloylated N-benzylidene -β-D-galactosylamine or N-benzylidene-α-D-arabinopyranosylamine. The process can also be performed by a one-pot procedure selectively giving (S)-aminophosphonic acid derivatives from galactosylamine and (R)-aminophosphonic acid derivatives from β-L-fucosylamine as the chiral auxiliaries.

  通过路易斯酸催化亚磷酸二乙酯与 O-新戊酰化 N-亚苄基-δ-D-半乳糖胺或 N-亚苄基-δ-D-阿拉伯吡喃糖基胺的加成，可立体选择性合成(S)-或(R)-δ-[(O-新戊酰-六吡喃糖基)氨基]苄基膦酸二乙酯。 该过程也可以通过单锅程序进行，选择性地从半乳糖胺中得到(S)-氨基膦酸衍生物，从δ²-L-岩藻糖胺中得到(R)-氨基膦酸衍生物作为手性助剂。
• Carbohydrates as chiral templates: Diastereoselective Ugi synthesis of (S)-amino acids using O-acylated D-arabinopyranosylamine as the auxiliary
  作者：Horst Kunz、Waldemar Pfrengle、Wilfried Sager

  DOI：10.1016/s0040-4039(00)99334-1

  日期：1989.1

  Enantiomerically pure (S)-amino acids are synthesized via a highly diastereoselective Ugi reaction using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine as the chiral template.

  对映体纯的（S）-氨基酸是通过高非对映选择性的Ugi反应合成的，使用2,3,4-三-O-新戊酰基-α-D-阿拉伯吡喃糖胺作为手性模板。
• Stereoselective Total Synthesis of the Diastereomeric Tricyclic Alkaloids Tetraponerine-7 and Tetraponerine-8 Using O-Pivalo­ylated d-Arabinopyranosylamine as the Common Auxiliary
  作者：Horst Kunz、Irina Strassnig、Karsten Körber、Udo Hünger

  DOI：10.1055/s-0034-1380215

  日期：——

  Based on a diastereoselective domino Mannich-Michael reaction cascade of 2-N-[(S)-3-(benzyloxycarbonyl)[4-(tert-butyldiphenylsiloxy)butyl]amino}octylidene]-2,3,4-tri-O-pivaloyl--d-arabinopyranosylamine with the Danishefsky diene, the major component of the neurotoxic venom of the New Guinean ant Tetraponera punctulata, tetraponerine-8, and its diastereomer tetraponerine-7 were synthesized in pure form. While the Mannich reaction of the arabinosyl imine of the required (S)-configured -aminoaldehyde gave the 2-substituted piperidinone precursor of tetraponerine-8 with excellent diastereoselectivity, the analogous Mannich reaction of the (R)-configured -aminoaldehyde afforded the precursor of tetraponerine-7 with a selectivity of only 2:1 (mismatched case). The enantiomerically pure tetraponerine-8, described as highly toxic for ants, exhibited only moderate toxicity to sucking and stinging insects.