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Toward the total synthesis of Sinefungin. 1982

Y Mizuno, and K Tsuchida, and H Tampo

Among many attempts toward the total synthesis of Sinefungin one of the most promising approach was found to be the transglycosylation of the amino acid-D-ribofuranosyl portion of 15 to N6-acyladenine. The key intermediate (15) was prepared from uridine in 12 steps. Thus, treatment of 2',3'-O-isopropylidene-uridine 5'-aldehyde (5) with methyl 4-nitrobutanoate gave rise to an aldol adduct (6) which was led to 4-nitro-4-(5'-deoxy-2', 3'-O-isopropylideneuridin-5'-yl)-butanal (10) via 8. A four-component condensation involving 10 afforded N,N-disubstituted alpha-aminocarboxamide derivative (11). The transglycosylation involving 8 and N6-benzoyladenine was successfully achieved. A parallel transglycosylation involving 15 and N6-benzoyladenine is under way to obtain 16.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D008722 Methods A series of steps taken in order to conduct research. Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D000241 Adenosine A nucleoside that is composed of ADENINE and D-RIBOSE. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. Adenocard,Adenoscan
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics

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