(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 | 75414-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (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
• 中文别名: 吡嗪,5-(1,2-二甲基丙基)-2,3-二甲基-
• 英文名称: (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one
• 英文别名: [(2S)-4-benzoyloxy-5-oxo-2H-pyran-2-yl]methyl benzoate
• CAS: 75414-38-9
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: DZROVXLEMVQGMW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  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 N-溴代丁二酰亚胺(NBS) 作用下， 生成 5-Benzoyloxy-2-benzoyloxymethyl-4H-pyran-4-on
  参考文献：
  名称：

  Lichtenthaler, Frieder W.; Jarglis, Pan; Hempe, Walter, Liebigs Annalen der Chemie, 1983, # 11, p. 1959 - 1972

  摘要：

  DOI：
• 作为产物：
  描述：

  1-脱氧-D-葡萄-己-1-烯桥吡喃糖四苯酸 在 吡啶 、 盐酸羟胺 、 盐酸 、 乙醛 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以84%的产率得到(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
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.01.019

文献信息

• A convenient access to 1,5-anhydroketoses
  作者：F.W. Lichtenthaler、E.S.H. El Ashry、V.H. Göckel

  DOI：10.1016/s0040-4039(00)92737-0

  日期：——

  A convenient, versatile entry into the 1,5-anhyroketose series is described and their conversion into enolones, enolone oximes and γ-pyrones.

  描述了一种方便，通用的进入1,5-脱水酮糖系列的方法，并将其转换为烯醇酮，烯醇酮肟和γ-吡喃酮。
• Structure of 1,5-Anhydro-D-fructose: X-ray Analysis of Crystalline Acetylated Dimeric Forms
  作者：Søren M. Andersen、Inge Lundt、Jan Marcussen、I. Søtofte、Shukun Yu

  DOI：10.1080/07328309808001881

  日期：1998.9.1

  Acetylation of 1,5-anhydro-D-fructose under acidic conditions gave two crystalline acetylated dimeric forms, which by X-ray analysis were shown to be diastereomeric spiroketals formed between C-2 and C-2/C-3. The structures of the compounds differed only at the configuration at C-2. Acetylation or benzoylation of 1,5-anhydro-D-fructose in pyridine yielded 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enos-2-ulopyra-nose or crystalline 1,5-anhydro-3,6-di-O-benzoyl-4-deoxy-D-glycero-hex-3-enos-2-ulo-pyranose.
• Brehm, Manfred; Dauben, William G.; Koehler, Peter, Angewandte Chemie, 1987, vol. 99, # 12, p. 1318 - 1319
  作者：Brehm, Manfred、Dauben, William G.、Koehler, Peter、Lichtenthaler, Frieder W.

  DOI：——

  日期：——
• Jarglis, Pan; Lichtenthaler, Frieder W., Angewandte Chemie, 1982, vol. 94, # 2, p. 140 - 141
  作者：Jarglis, Pan、Lichtenthaler, Frieder W.

  DOI：——

  日期：——
• BREHM, MANFRED;DAUBEN, WILLIAM G.;KOHLER, PETER;LICHTENTHALER, FRIEDER W., ANGEW. CHEM., 99,(1987) N 12, 1318-1319
  作者：BREHM, MANFRED、DAUBEN, WILLIAM G.、KOHLER, PETER、LICHTENTHALER, FRIEDER W.

  DOI：——

  日期：——