(S,S)-Palythazin | 72681-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (S,S)-Palythazin
• 英文别名: (3S,8S)-1,3,4,6,8,9-hexahydrodipyrano[3,4-b:3',4'-e]pyrazine-3,8-dimethanol；(S,S)-palythazine；palythazine；Palythazin；((3S)-1,3,4,6,8,9-hexahydro-dipyrano[3,4-b;3',4'-e]pyrazine-3r,8c-diyl)-bis-methanol；(3S)-3r,8c-bis-hydroxymethyl-1,3,4,6,8,9-hexahydro-dipyrano[3,4-b;3',4'-e]pyrazine；[(6S,13S)-13-(hydroxymethyl)-5,12-dioxa-2,9-diazatricyclo[8.4.0.03,8]tetradeca-1,3(8),9-trien-6-yl]methanol
• CAS: 72681-96-0
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: FDOHUZKENKIHJT-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (6S)-6-[(苯甲酰氧基)甲基]-3-氧代-3,6-二氢-2H-吡喃-4-基苯甲酸酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 甲醇 、 air 、 盐酸羟胺 、 氢气 、 sodium methylate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 15.0h， 生成 (S,S)-Palythazin
  参考文献：
  名称：

  Jarglis, Pan; Lichtenthaler, Frieder W., Angewandte Chemie, 1982, vol. 94, # 2, p. 140 - 141

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of (S,S)-palythazine from d-mannitol
  作者：Kommu Nagaiah、Khandregula Srinivasu、S. Praveen Kumar、Jeelani Basha、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2010.05.002

  日期：2010.4

  Exploiting the symmetry element, an asymmetric synthesis of (S,S)-palythazine was accomplished with (R)-glyceraldehyde acetonide as the chiral precursor The prominent steps involved stereoselective Barbier allylation, ring-closing metathesis. regioselective nucleophilic opening of epoxide. and auto-condensation of aminoketone moiety (C) 2010 Elsevier Ltd. All rights reserved
• Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (−)-bissetone and (−)-palythazine
  作者：Manfred Brehm、Volker H. Göckel、Pan Jarglis、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2008.01.019

  日期：2008.2

  High-yielding protocols are described to convert D-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and beta-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-D-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale. (C) 2008 Elsevier Ltd. All rights reserved.