(2R)-glycidyl triflate | 143169-39-5

• 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: (2R)-glycidyl triflate
• 英文别名: Trifluoromethanesulfonic acid (R)-glycidyl ester；[(2R)-oxiran-2-yl]methyl trifluoromethanesulfonate
• CAS: 143169-39-5
• 化学式: C₄H₅F₃O₄S
• 分子量: 206.143
• InChiKey: IBFRBNCRKBAISE-GSVOUGTGSA-N

物化性质

• 沸点：
  188.9±35.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-glycidyl triflate 、 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到[(R)-1-(1-Benzenesulfonyl-2-hydroxymethyl-cyclopropyl)-2-(tetrahydro-pyran-2-yloxy)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropane α-amino acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-methanoproline and N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid

  摘要：

  The tide compounds were synthesized by a S-step facile transformation of the key intermediate 4, itself obtained by a ''one-pot'' sulfone-mediated cyclopropanation from chiral synthon (R)-I and (2R)-glycidyl triflate.

  DOI：

  10.1016/0040-4039(95)00482-r

文献信息

• A novel method for chirospecific synthesis of 2,5-disubstituted pyrrolidines
  作者：N. André Sasaki、Isabelle Sagnard

  DOI：10.1016/s0040-4020(01)85236-4

  日期：1994.1

  One-pot ring formation using (R)-1 or (S)-1 as a nucleophile and homochiral glycidyl triflate (R)-2 or (S)-2 as an electrophile a pivotal intermediate 4 which can be transformed into a 2,5-disubstituted pyrrolidine with any desired stereochemistry at the C-2 and C-5 positions.

  一锅环的形成使用（R） - 1或（S） - 1作为亲核和纯手性缩水甘油基三氟甲磺酸酯（R） - 2或（S） - 2作为亲电子试剂的枢转中间体4可转化成2， 5-二取代的吡咯烷在C-2和C-5位置具有任何所需的立体化学。
• Phase-transfer-catalyzed Asymmetric Alkylation with Epoxy Triflates as Alkylating Agents: Highly Stereoselective Synthesis of γ,δ-Epoxy-α-amino Acids
  作者：Satoru Arimitsu、Daisuke Kato、Keiji Maruoka

  DOI：10.1246/cl.2011.1115

  日期：2011.10.5

  Although alkyl sulfonates are commonly used for alkylating agents, there are very few reports on phase-transfer-catalyzed asymmetric alkylation with alkyl sulfonates. Herein, we report that the asy...

  尽管烷基磺酸盐通常用于烷基化剂，但很少有关于相转移催化的烷基磺酸盐不对称烷基化的报道。在这里，我们报告说，asy...
• Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized<i>C</i>-Glycosides
  作者：Baudouin Gerard、Maurice D. Lee、Sivaraman Dandapani、Jeremy R. Duvall、Mark E. Fitzgerald、Sarathy Kesavan、Jason T. Lowe、Jean-Charles Marié、Bhaumik A. Pandya、Byung-Chul Suh、Morgan Welzel O’Shea、Michael Dombrowski、Diane Hamann、Berenice Lemercier、Tiffanie Murillo、Lakshmi B. Akella、Michael A. Foley、Lisa A. Marcaurelle

  DOI：10.1021/jo4000916

  日期：2013.6.7

  A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis

  开发了一种面向多样性的合成 (DOS) 策略，用于合成包含吡喃部分的立体化学多样化的稠环系统。每个支架都含有胺和甲酯，用于通过胺封端和酰胺偶联进一步多样化。通过基于形状的主惯性矩 (PMI) 分析，与先前制备的支架相比，对支架多样性进行了评估。
• Design of Bifunctional Antibiotics that Target Bacterial rRNA and Inhibit Resistance-Causing Enzymes
  作者：Steven J. Sucheck、Andrew L. Wong、Kathryn M. Koeller、David D. Boehr、Kari-ann Draker、Pamela Sears、Gerard D. Wright、Chi-Huey Wong

  DOI：10.1021/ja000575w

  日期：2000.5.1
• Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine
  作者：Kevin Burgess、Kwok Kan Ho

  DOI：10.1021/jo00048a028

  日期：1992.10

  Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine ((Z)- and (E)-cyclo-Met) are described. The source of chirality in these reactions is the trifluoromethylsulfonate ester 1b which reacts with di-tert-butyl malonate via direct displacement of trifluoromethylsulfonate followed by lactonization to give 1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo[3.1.0]hexane (2). Conversion of compound 2 into (Z)-cyclo-Met can be achieved via ring opening of the lactone, Hoffmann rearrangement, mesylation, and displacement with thiomethoxide. A route to (E)-cyclo-Met was developed using a lipase to effect a critical ester hydrolysis.