(S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone | 130481-72-0

• 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: (S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone
• 英文别名: [(2S,4aR,7R,7aS)-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate
• CAS: 130481-72-0
• 化学式: C₁₃H₁₁F₃O₇S
• 分子量: 368.287
• InChiKey: GRXYGPCXNHKDSX-KLBPJQLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 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：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone 在 lead(IV) acetate 、 sodium hydroxide 、 N-氯代丁二酰亚胺 、 18-冠醚-6 、 potassium carbonate 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 9-(2,4-O(R)-benzylidene-β-D-threo-oxetanosyl)adenine
  参考文献：
  名称：

  Synthesis of the potent antiviral oxetane nucleoside epinoroxetanocin from D-lyxonolactone

  摘要：

  DOI：

  10.1016/s0957-4166(00)80541-8
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 溴 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone
  参考文献：
  名称：

  cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: hexamers of oxetane cis-β-amino acids

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00660-8

文献信息

• Kruelle, Thomas M.; Davis, Benjamin; Ardron, Helen, Journal of the Chemical Society. Chemical communications, 1996, # 11, p. 1271 - 1272
  作者：Kruelle, Thomas M.、Davis, Benjamin、Ardron, Helen、Long, Daniel D.、Hindle, Neil A.、et al.

  DOI：——

  日期：——
• 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.
• High yield reduction of 2-O-trifluoromethanesulphonate esters of α-hydroxylactones to the corresponding 2-deoxylactones by lithium iodide trihydrate
  作者：Russell P. Elliott、George W.J. Fleet、Soo Gyoung Young、Nigel G. Ramsden、Colin Smith

  DOI：10.1016/s0040-4039(00)97471-9

  日期：——
• 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