5-amino-5-deoxy-, derivative, synthesis

Amino-%-deoxy derivative of Mode of synthesis Melting point, °C. Hydrochloride ... 

The amino nitrile synthesis is particularly useful for the preparation of 2-amino-2-deoxy derivatives of rare sugars which would be difficult to obtain as intermediates in a synthesis involving animation alone. Thus, 2-amino-2-deoxy-L-glucose and 2-amino-2-deoxy-L-mannose can be prepared in good yield from the readily available L-arabinose.11,18... 

A variety of amino-alcohol derivatives have been used as substrates for RCM approaches to piperidines. Representative examples of these methods are shown in Scheme 18 (32, <01TL1209> 33, <01TA817> 34, <02OL4499). Application of this chemistry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines has been reported <01TL4079>. 

Toward a complete synthesis of trehazolin (2), 2,3,4,6-tetra-O-benzyl-1 -deoxy-z-D-glucopyranosyl isothiocyanate (7)52 was brought into reaction with the amines 5 and 374 in the presence of triethylamine to afford the x-D-glucopyranosyl thiourea derivatives 375 or 376, respectively (Scheme 46).38 Subsequent treatment with 2-chloro-3-ethylbenzoxazolium tetrafluoroborate and triethylamine afforded the corresponding amino oxazoline derivatives 377 and 378. Finally, hydrogenation over Pd(OH)2 on carbon afforded trehazolin (2). 

Fortimicin B has been converted to dactimicin (391) by selective formimidation of the 2"-amino group with formimidate hydrochloride in dry ethanol [225]. Another report described the synthesis of a number of fortimicin KG2 analogs, including 3,4-didemethyl, 4-demethyl, and 3-amino-4-demethoxy-4-deoxy derivatives from sis-amine [226]. 

W. Meyer zu Reckendorf and W. A. Boimer, Sulfur substitution products of amino sugars. VI. Synthesis of 2-amino-2-deoxy-3-thio-D-allose derivatives through thiazoline intermediates. Tetrahedron, 19 (1963) 1721-1725. 

It is known that deamination of some readily available amino acids can be performed with nearly quantitative retention of configuration. Based on this conversion, Yamada and co-workers elaborated an ingenious synthesis of o-ribose and D-lyxose starting from L-glutamic acid. The preliminary communication of this work was reported in the first volume of Ais series.Now the full details have been published. In an extension of the application of the unsaturated intermediate (399) for the synthesis of other pentoses, all 2,3-anhydro derivatives (400-403) were prepared. LAH-Reduction of -D-ribo and o-D-lyxo epoxides (400 and 401) afforded, after acetylation, 3-deoxy-pentosides 404 and 405, whereas the same reaction conditions converted fi-D-lyxo a-D-ribo epoxides (402 and 403) into the corresponding 2-deoxy-derivatives (406 and 407). 

The furoisoxazoline (8) has been used for the total synthesis of amino-deoxy pentose and pentitol derivatives, synthesis of the latter being outlined in Scheme 5. ... 

The purine nucleotides GTP and ATP are very important in intermediary metabolism and the regulation of metabolism. Adenine is also a component of cyclic AMP, FAD, NAD, NADP and coenzyme A. Moreover, GTP, ATP and their deoxy derivatives dGTP and dATP are important precursors for the synthesis of RNA and DNA respectively, which are essential for cell growth and division. Purine biosynthesis (Fig. 59.1) needs the amino acids giutamine, giycine and aspartate. Also, tryptophan is needed to supply formate which reacts with tet-rahydrofolate (THF) to produce A "-formyl THF, which donates the formyl group to the purine structure. A molecule of CO2 is also needed. 

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