methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate | 322726-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate
• 英文别名: methyl 2,4-anhydro-3,5-(R)-O-benzylidene-L-rhamnonate；methyl (1R,3R,5S,6S,8R)-5-methyl-3-phenyl-2,4,7-trioxabicyclo[4.2.0]octane-8-carboxylate
• CAS: 322726-61-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: CSQXSEVLUFGWHJ-QTSITOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 barium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 二甲基亚砜 为溶剂， 反应 39.0h， 生成 (2R,3R,4S)-4-[(1S)-1-azidoethyl]-3-hydroxyoxetane-2-carboxylic acid
  参考文献：
  名称：

  Pseudoenantiomeric oxetane δ-amino acid scaffolds derived from L-rhamnose and D-xylose: D/L-alanine-D-serine and glycine-L-serine dipeptide isosteres

  摘要：

  A series of oxetane delta-amino acid scaffolds derived from L-rhamnose and D-xylose provide a new class of templated sugar amino acids (SAA), which can be considered as D/L-alanine-D-serine and glycine-L-serine dipeptide isosteres. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.023
• 作为产物：
  描述：

  L-rhamnopyranose 在 吡啶 、 溴 、 potassium carbonate 、 barium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 50.5h， 生成 methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate
  参考文献：
  名称：

  Oxetane cis- and trans-β-amino-acid scaffolds from l-rhamnose by efficient SN2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin

  摘要：

  An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from L-rhamnose-with retention of configuration in the ring closure-is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an oxetane cis-beta-amino acid. Subsequent nucleophilic displacements of the corresponding triflates by azide proceed in consistently excellent yields, without any elimination, to provide syntheses of scaffolds for analogues of the antibiotic. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.032

文献信息

• cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: hexamers of oxetane cis-β-amino acids
  作者：Sarah F Barker、Donald Angus、Claude Taillefumier、Michael R Probert、David J Watkin、Mark P Watterson、Timothy D.W Claridge、Natasha L Hungerford、George W.J Fleet

  DOI：10.1016/s0040-4039(01)00660-8

  日期：2001.6

  Efficient synthesis of both cis- and trans-3-azido-oxktane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-beta-amino acids into oligomers; the synthesis of a series of protected beta-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate are reported. (C) 2001 Elsevier Science Ltd. AII rights reserved.
• Two epimerisations in the formation of oxetanes from l-rhamnose: towards oxetane-containing peptidomimetics
  作者：Stephen W Johnson、Donald Angus、Claude Taillefumier、John H Jones、David J Watkin、Emma Floyd、J.Grant Buchanan、George W.J Fleet

  DOI：10.1016/s0957-4166(00)00360-8

  日期：2000.10

  The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane beta -amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Pseudoenantiomeric oxetane δ-amino acid scaffolds derived from L-rhamnose and D-xylose: D/L-alanine-D-serine and glycine-L-serine dipeptide isosteres
  作者：Stephen W. Johnson、Sarah. F. Jenkinson (née Barker)、Donald Angus、John H. Jones、David J. Watkin、George W.J. Fleet

  DOI：10.1016/j.tetasy.2004.08.023

  日期：2004.10

  A series of oxetane delta-amino acid scaffolds derived from L-rhamnose and D-xylose provide a new class of templated sugar amino acids (SAA), which can be considered as D/L-alanine-D-serine and glycine-L-serine dipeptide isosteres. (C) 2004 Elsevier Ltd. All rights reserved.
• Oxetane cis- and trans-β-amino-acid scaffolds from l-rhamnose by efficient SN2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin
  作者：Stephen W. Johnson、Sarah F. Jenkinson (née Barker)、Donald Angus、John H. Jones、George W.J. Fleet、Claude Taillefumier

  DOI：10.1016/j.tetasy.2004.07.032

  日期：2004.9

  An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from L-rhamnose-with retention of configuration in the ring closure-is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an oxetane cis-beta-amino acid. Subsequent nucleophilic displacements of the corresponding triflates by azide proceed in consistently excellent yields, without any elimination, to provide syntheses of scaffolds for analogues of the antibiotic. (C) 2004 Elsevier Ltd. All rights reserved.