Синтез новых производных ?-трифторметилзамещенных ?-аминокислот и их мультифункциональных аналогов
Диссертация
Впервые разработан эффективный метод синтеза диэтил-1-диазо-2,2,2-трифторэтилфосфоната — первого представителя фторсодержащих а-диазофосфонатов. Изучены его свойства в металлокатализируемых реакциях внедрения по ОНи NH-связям первичных спиртов и аминов. Разработан эффективный метод синтеза диэтил-1-диазо-2,2,2-трифторэтил-фосфоната — первого представителя фторсодержащих а-диазофосфонатов. Изучены… Читать ещё >
Содержание
- Глава I. ЛИТЕРАТУРНЫЙ ОБЗОР. a-CF3-a-Аминокислоты: синтез и введение в пептиды"
- Предисловие
- 1. 1. Синтез СРз-содержащих аминокислот на основе иминов алкилтрифторпируватов
- 1. 1. 1. Синтез иминов
- 1. 1. 2. Восстановление иминов
- 1. 1. 3. Присоединение С-нуклеофилов к иминам
- 1. 1. 4. Реакция иминов с енолятами титана
- 1. 1. 5. Нерацемический синтез трифторметилсодержащего пролина
- 1. 2. Реакция Штрекера
- 1. 3. Ацилирование СРз-азиридинов
- 1. 4. Трансформация функциональных групп
- 1. 4. 1. Синтез CFз-аминокислот из енаминофосфонатов
- 1. 4. 2. Асимметрический синтез 3,3,3-трифтораланина из 2,2,2-трифтор-! -фуран-2-ил-этанона
- 1. 4. 3. Восстановление CF^-содержащих N-apwi-fi-сульфинилгшинов
- 1. 5. Пептидный синтез
- 1. 5. 1. Введение a-CFз-а-аминокислот в N-терминальную позицию пептидов
- 1. 5. 2. Введение a-CF з-а-аминокислот в С-терминальную позицию пептидов
- 1. 5. 3. Ферментативный синтез
- 1. 1. Синтез СРз-содержащих аминокислот на основе иминов алкилтрифторпируватов
- 2. 1. Синтез а-СРз-замещенных а-аминокислот с N-оксалильной и N-фосфоноформильной группами
- 2. 1. 1. Синтез N-оксалил- и N-фосфоноформилиминов метилтрифторпирувата
- 2. 1. 2. Реакции иминов с С-нуклеофилами
- 2. 1. 3. Реакции иминов с ароматическими ж-донорами
- 2. 1. 4. Восстановление иминов
- 2. 2. а-Диазокарбоксилаты и а-диазофосфонаты в синтезе трифторметилзамещенных а-аминокислот и их функциональных аналогов
- 2. 2. 1. Синтез трифторметшсодержащих депсипептидов из 3,3,3-трифтор-2-диазопропионата
- 2. 2. 2. Синтез трифторметшсодержащих а-гидрокси и а-амиио-фосфонатов из диэтил-1-диазо-2,2,2-трифторэтил-фосфоната
- 2. 2. 3. Сигматропные перегруппировки илидов азота в синтезе CF3-замещенных производных а-аминокарбоновых и а-аминофосфоновых кислот
- 2. 2. 4. Сигматропные перегруппировки илидов серы в синтезе CFj-замещенных производных а-алкштиокарбоновых и а-алкилтиофосфоновых кислот
- 2. 3. а-СРз-замещенные карбоксилаты и фосфонаты, содержащие 1,2,3триазольный фрагмент
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