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The sulfonyl phosphonomethoxy hybrid peptide synthesis and ohmefentanyl asymmetric synthesis

Author: HeFengDan
Tutor: HuWenXiang；XuJiaXi
School: Capital Normal University
Course: Analytical Chemistry
Keywords: hybrid sulfonophosphonopeptides mechanism Asymmetric Synthesis Ohmefentanyl
CLC: TQ464.7
Type: Master's thesis
Year: 2009
Downloads: 57
Quote: 0
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Abstract


The first part of the work is the synthesis of hybrid sulfonophosphonopeptides:Sulfonopeptides include partial sulfonopeptides and complete sulfonopeptides. When peptidescontaining one or more aminophosphonic acid components were called phosphonopeptides, aclass of unnatural compounds containing a tetrahedral phosphorus atom. The sulfonopeptidespossessing tetrahedral sulfonamide moiety can be used to mimic transition state analogues ofhydrolysis in the ester and amide bonds. As phosphorus and sulfur ananlogues of peptides, theywere both widely used as enzyme inhibitors and heptans for inducing catalytic antibodies.Moreover, they are both unnatural peptides, can only be synthesized by chemical methods.Becauseα-sulfonopeptides are unstable, Current studies mainly focus on synthesizing?-sulfonopeptides that the structure was similar whith general peptides. But at present still haveno other effective methods to form sulfonamide bound except used sulfonyl chloride or thesulfinyl chloride as intermediate; There are a lot of routs to prepare phosphonopeptides, in whichMannich-type reaction is the simplest synthetic method; Untill now still have no documents toreport the synthetic method of hybrid sulfonophosphonopeptide. In this dissertation, the methodof hybrid sulfonophosphonopeptide has been explored.Various N-propected amino sulfonamide have been synthesized in excellent yields fromamino alcohols via esterification, nucleophilic substitution to give amino sulfonic acid, thenamino was protected by Cbz-Cl and sulfonyl chloride obtained by SOCl2 following aminolysis inammonia waterA simple, efficent and general method has been developed for the preparation of hybridsulfonophosphonopeptides through one-pot reaction under solvent conditions then aminolysiswhith Amino acid esters or their salts. In summary, 12 new sulfonamide compounds containingN-P bound have been synthesized, and their structures were confirmed by IR, 1H NMR, 13CNMR and HRMS.The second part of the work is the asymmetric synthesis of Ohmefentanyl. 1-benzyl-3-methyl-4-piperidone was prepared from benzylamine, methyl methacrylate and the methyl acrylate viaMicheal addition, Dieckmann condensation and decarboxylation reaction in an overall yield of40%. A new potent and ultra short acting narcotic analgesic Ohmefentanyl were prepared from1-benzyl-3-methyl-4-piperidone through amination condensation, resolution, hydrolysis,propionylation, debenzylation and so on.

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Drug production of biological products > Amino acids,peptides,proteins
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