methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-lyxonate | 134651-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-lyxonate
• 英文别名: methyl (2S,3S,4R)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(trifluoromethylsulfonyloxy)oxetane-2-carboxylate
• CAS: 134651-23-3
• 化学式: C₂₃H₂₇F₃O₇SSi
• 分子量: 532.61
• InChiKey: FAEOAARATNXHBY-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-lyxonate 在 sodium azide 作用下， 以 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-木糖酸-gamma-内酯 在 吡啶 、 咪唑 、 盐酸 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.25h， 生成 methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-lyxonate
  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

• Synthesis and structure-activity relationships of some novel oxetane carbapenems
  作者：Subas M. Sakya、Timothy W. Strohmeyer、Panayota Bitha、Stanley A. Lang、Yang-I Lin

  DOI：10.1016/s0960-894x(97)00280-1

  日期：1997.7

  Six disubstituted oxetane carbapenems were synthesized and their antibacterial profile compared with the lead amino methyl THF carbapenem as well as imipenem. The oxetane carbapenems had comparable or less activity against the Gram(-) bacteria and had reduced activity against Gram(+) bacteria in comparison with imipenem and the THF carbapenem CL 191,121, but were highly stable to hydrolysis by hog kidney dehydropeptidase (DHP). (C) 1997 Elsevier Science Ltd.
• 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.