[(2S,4aR,7S,7aS)-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate | 130481-71-9

• 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: [(2S,4aR,7S,7aS)-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate
• CAS: 130481-71-9
• 化学式: C₁₃H₁₁F₃O₇S
• 分子量: 368.287
• InChiKey: GRXYGPCXNHKDSX-WDCWCFNPSA-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：

  [(2S,4aR,7S,7aS)-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate 在 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到(2S,4aR,7aR)-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
  参考文献：
  名称：

  High yield reduction of 2-O-trifluoromethanesulphonate esters of α-hydroxylactones to the corresponding 2-deoxylactones by lithium iodide trihydrate

  摘要：

  DOI：

  10.1016/s0040-4039(00)97471-9
• 作为产物：
  描述：

  苯甲醛 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 2.5h， 生成 [(2S,4aR,7S,7aS)-6-oxo-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

  摘要：

  摘要 2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-核糖醇（DRBNAc）和对映体 LRBNAc 分别由 L- 和 D-lyxonolactone 制备而成，是潜在的己糖胺酸酶抑制剂。无论是 N-苄基-DRBNAc 还是 N-苄基-LRBNAc，都没有显示出对 α 或 β-己糖胺酶或任何其他糖苷酶的抑制作用。

  DOI：

  10.1016/j.crci.2010.03.020

文献信息

• Design and Synthesis of Orthogonally Protected <scp>d</scp>- and <scp>l</scp>-β-Hydroxyenduracididines from <scp>d</scp>-<i>lyxono</i>-1,4-Lactone
  作者：Cheng-Kun Lin、Chung-Chien Hou、Yi-Yong Guo、Wei-Chieh Cheng

  DOI：10.1021/acs.orglett.6b02444

  日期：2016.10.21

  A practical synthesis of the orthogonally protected d- and l-β-hydroxyenduracididines (d- and l-βhEnds), the unique, nonproteinogenic α-amino acids found in mannopeptimycin antibiotics, is described. We appropriately applied d-lyxono-1,4-lactone derivatives as a starting template and investigated two transformations: (i) reduction of the lactone in a two-step sequence and (ii) regioselective ring opening

  描述了一种实用合成的正交保护的d-和l -β-羟基神经尿苷（d-和l- βhEnds），这是在甘露肽霉素抗生素中发现的独特的，非蛋白原性的α-氨基酸。我们适当地将d - lyxono -1,4-内酯衍生物用作起始模板，并研究了两种转化：（i）以两步顺序还原内酯，以及（ii）亚苄基乙缩醛的区域选择性开环。通过仔细评估反应条件，成功制备了多克量的正交保护的d-和l- βhEnds。
• 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：——
• Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
  作者：J.S.Shane Rountree、Terry D. Butters、Mark R. Wormald、Raymond A. Dwek、Naoki Asano、Kyoko Ikeda、Emma L. Evinson、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/j.tetlet.2007.04.041

  日期：2007.6

  The synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideOXY-L-arabinitoI LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol DABNAc, was prepared from L-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors Of D-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while Dimino sugar mimics inhibit D-glycohydrolases competitively, their L-enantiomers show non-competitive inhibition and in the case of iminofuranoses L-enantiomers are usually more potent inhibitors. (c) 2007 Elsevier Ltd. All 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