2,4-脱水-3,5-O-[(S)-苯基亚甲基]-D-来苏糖酸甲酯 | 131550-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 中文名称: 2,4-脱水-3,5-O-[(S)-苯基亚甲基]-D-来苏糖酸甲酯
• 英文名称: methyl 2,4-anhydro-(S)-3,5-benzylidene-D-lyxonate
• 英文别名: methyl (1S,3S,6R,8S)-3-phenyl-2,4,7-trioxabicyclo[4.2.0]octane-8-carboxylate
• CAS: 131550-06-6
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: YLWSGWORUDULID-BLFANLJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2,4-脱水-3,5-O-[(S)-苯基亚甲基]-D-来苏糖酸甲酯 在 钯 吡啶 、 咪唑 、 sodium azide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,3R,4S)-3-azido-4-[[tert-butyl(diphenyl)silyl]oxymethyl]oxetane-2-carboxylate
  参考文献：
  名称：

  Oxetane nucleosides with fluorine and azide substitutents: nucleophilic displacements on an oxetane ring

  摘要：

  Flourine and azide substituents are introduced into an oxetane ring by nucleophilic displacement reactions; the syntheses and anti-viral activities of 9-(2'-azido-2'-deoxy-beta-D-erythro-oxetanosyl)-adenine and of 9-(2'-deoxy-2'-fluoro-beta-D-erythro-oxetanosyl)-adenine are reported.

  DOI：

  10.1016/s0040-4039(00)74302-4
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 盐酸 、 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.25h， 生成 2,4-脱水-3,5-O-[(S)-苯基亚甲基]-D-来苏糖酸甲酯
  参考文献：
  名称：

  Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid

  摘要：

  Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subsequent nucleophilic displacements of the corresponding triflates by azide proceeds in consistently excellent yields without any elimination to provide syntheses of scaffolds for a range of methyl and hydroxymethyl analogues of the antibiotic oxetin, a naturally occurring oxetane cis-beta-amino acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.031

文献信息

• 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.
• 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.
• Synthesis of the potent antiviral oxetane nucleoside epinoroxetanocin from D-lyxonolactone
  作者：Y. Wang、G.W.J. Fleet、R. Storer、P.L. Myers、C.J. Wallis、O. Doherty、D.J. Watkin、K. Vogt、D.R. Witty、F.X. Wilson、J.M. Peach

  DOI：10.1016/s0957-4166(00)80541-8

  日期：1990.1
• Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid
  作者：Sarah F. Jenkinson (née Barker)、Timothy Harris、George W.J. Fleet

  DOI：10.1016/j.tetasy.2004.07.031

  日期：2004.9

  Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subsequent nucleophilic displacements of the corresponding triflates by azide proceeds in consistently excellent yields without any elimination to provide syntheses of scaffolds for a range of methyl and hydroxymethyl analogues of the antibiotic oxetin, a naturally occurring oxetane cis-beta-amino acid. (C) 2004 Elsevier Ltd. All rights reserved.
• Oxetane nucleosides with fluorine and azide substitutents: nucleophilic displacements on an oxetane ring
  作者：Y. Wang、G.W.J. Fleet、F.X. Wilson、R. Storer、C.J. Wallis、O. Doherty、D.J. Watkin、K. Vogt、D.R. Witty、J.M. Peach

  DOI：10.1016/s0040-4039(00)74302-4

  日期：1991.3

  Flourine and azide substituents are introduced into an oxetane ring by nucleophilic displacement reactions; the syntheses and anti-viral activities of 9-(2'-azido-2'-deoxy-beta-D-erythro-oxetanosyl)-adenine and of 9-(2'-deoxy-2'-fluoro-beta-D-erythro-oxetanosyl)-adenine are reported.