209115-33-3Relevant academic research and scientific papers
Synthesis and Structural Elucidation of 1,2-Disubstituted 3-Fluoropiperidines
Evans, Paul,Fischer, Pauline,Müller-Bunz, Helge,Morris, Morgan
, (2020/02/28)
The work described details the reaction between Selectfluor and a series of 1-carbonyloxy and 1-sulfonyl 2-piperidines in order to generate 3-fluoro-2-methoxypiperidines 3a–f. Their subsequent reaction with allyltrimethylsilane, in the presence of BF3 and TiCl4, is then reported. Studies involving a combination of single-crystal X-ray crystallography and NMR spectroscopy indicate that the allylation process is cis-selective for both carbamate and sulfonamide variants and that optimal levels of diastereoselectivity are obtained using the N-2-nitrobenzene sulfonyl (2-Ns) group. In this manner, the synthesis of a series of 2-allyl 3-fluoro-substituted piperidines (5a, c–f) was achieved. The conversion of both the cis and trans-N-tosyl adducts (5d) into 3-fluorinated analogues of the natural products pelletierine (10) and coniine (11) is subsequently detailed.
Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions
Park, Heemin,Kwon, Yongseok,Shin, Jae Eui,Kim, Woo-Jung,Hwang, Soonho,Lee, Seokwoo,Kim, Sanghee
supporting information, p. 2761 - 2767 (2017/06/13)
The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction involves the activation of the hydroxyl group via the use of orthoesters. Despite the reduced nucleophilicity of carbamate nitrogen, this reaction system provides several types of pyrrolidines and piperidines in good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.
A facile synthesis of ω-aminoalkyl ammonium hydrogen phosphates
Kong, Wei Bo,Zhou, Xiao Yong,Yang, Yang,Xie, Xing Yi
experimental part, p. 923 - 926 (2012/09/21)
A series of ω-aminoalkyl ammonium hydrogen phosphates were synthesized through a simple and efficient three-step method. The starting materials, ω-aminoalkyl alcohols (AC-n, with carbon number n = 3, 4, 5, 6), were amino-protected with 9-fluorenylmethyl chloroformate (Fmoc-Cl), followed by phosphorylation with POCl3 and deprotection in piperidine/DMF. The structures of each intermediate and final product were confirmed by 1H NMR, FTIR and mass spectrum. The yield of each step was about 77-92%, with a total yield higher than 56%. This new method was superior in low-cost raw materials, mild reaction temperatures (0-25°C) and easy purification methods.
A versatile annulation protocol toward novel constrained phosphinic peptidomimetics
Nasopoulou, Magdalini,Georgiadis, Dimitris,Matziari, Magdalini,Dive, Vincent,Yiotakis, Athanasios
, p. 7222 - 7228 (2008/02/12)
(Chemical Equation Presented) The development of a novel 3-center 2-component annulation reaction between α,ω-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting α,ω-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.
Preparation of high-loading polymer supports by polymerization reaction useful for oligonucleotide synthesis
Manchanda, Romila,Agarwal, Sunil K.,Kumar, Pradeep,Sharma, Ashwani K.,Gupta, Kailash C.,Chandra, Ramesh
, p. 2754 - 2762 (2007/10/03)
A simple protocol based on polymerization reactions has been developed for the preparation of high-loading polymer supports, useful for large-scale synthesis of oligonucleotides. Polymer supports of different pore sizes have been employed in the present i
Synthesis of chiral peptide nucleic acids using Fmoc chemistry
Wu, Yun,Xu, Jie-Cheng
, p. 8107 - 8113 (2007/10/03)
A Fmoc-based synthesis of chiral PNAs is described. Chiral monomer backbones were efficiently prepared by reductive amination of N-Fmoc-protected L,D-alaninals with glycine esters and the subsequent acylation of free amines with thymine-1-ylacetic acid. T
The Synthesis of Oxa-Analogues and Homologues of Naturally Occuring Polyamines
Lin, P. Kong Thoo,Kuksa, V. A.,Maguire, N. M.
, p. 859 - 866 (2007/10/03)
A number of polyamine oxa-analogues 14a-d, 19 have been synthesized.Spermidine oxa-analogues and homologues 14 were made from N-(aminooxypropyl)phthalimide 8a which was obtained either from the Fmoc-deprotection of N-phthalimide 4a or from the reaction between 3-bromopropylamine and N-hydroxyphthalimide, both reactions involving an unusual rearrangement mechanism.Sulphonated derivatives 9, 16, upon Mitsunobu condensation with N-protected 3-aminopropanol or N-alkylation with N-(bromoalkyl)phthalimides, afforded the fully protected spermidine and spermine oxa-analogues.Subsequent sequential deprotection gave spermidine analogues 14.Using the same strategy, spermine oxa-analogues 19 was synthesised. - Keywords: polyamines; oxa-analogues of polyamines; polyamine homologues; rearrangement; synthesis
