(2S,3S)-3-azido-5-methylhexane-1,2-diol | 154913-79-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S,3S)-3-azido-5-methylhexane-1,2-diol
• CAS: 154913-79-8
• 化学式: C₇H₁₅N₃O₂
• 分子量: 173.215
• InChiKey: FVMDGEWRMDVXFK-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.22
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-5-methylhexane-1,2-diol 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 氢气 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-(tert-butoxycarbonylamino)-5-methyl-1-methylsulfonyl-2-hexanol
  参考文献：
  名称：

  Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones

  摘要：

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.

  DOI：

  10.1021/jo0268456
• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-5-methyl-1-hexanol 在 盐酸 、 叠氮化锂 、 lithium perchlorate 、 苦味酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.5h， 生成 (2S,3S)-3-azido-5-methylhexane-1,2-diol
  参考文献：
  名称：

  Bertelli, Lucia; Fiaschi, Rita; Napolitano, Elio, Gazzetta Chimica Italiana, 1993, vol. 123, # 9, p. 521 - 524

  摘要：

  DOI：

文献信息

• A General, Catalytic, and Enantioselective Synthesis of (<i>S</i>)-γ-[(<i>S</i>)-1-Aminoalkyl]-γ-lactones
  作者：Núria Aguilar、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo9720851

  日期：1998.5.1

  A catalytic asymmetric synthesis of N-phthaloyl (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones, widely used intermediates in the preparation of hydroxyethylene dipeptide isosteres, is described. The highly enantiopure epoxy alcohols arising from the Sharpless epoxidation of (E)-allyl alcohols are first converted to (S)-N-phthaloyl-[(S)-1-aminoalkyl]oxiranes by means of an efficient four-step sequence involving the regio- and stereoselective ring opening of the starting epoxide by azide, reduction, phthaloylation, and intramolecular Mitsunobu cyclization of the intermediate phthalimido diol. Treatment of the resulting oxirane with lithium (1R)-menthyloxyacetylide in the presence of boron trifluoride etherate, followed by in situ hydrolysis of the ynol ether, leads to a (4R, 5S)-5-phthalimido-4-hydroxy ester. A Mitsunobu reaction with p-nitrobenzoic acid (which establishes the correct (S)configuration at C-4) and subsequent selective saponification of the benzoate and cyclization of the inverted hydroxy ester afford the target N-protected (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones. Using this methodology, lactones 19 and 26 were obtained in seven steps from the readily available epoxy alcohols 5 and 20, respectively, in high enantiomeric purity.