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Original scientific paper

Synthesis and Chemical Behaviour of a- and B-D-Glucopyranosyl Esters of L-Serine and Their Derivatives

Š. Valenteković ; Tracer Laboratory, Department of Organic Chemistry and Biochemistry, »Ruder Boskovic« Institute, POB' 1016, 41001, Zagreb, Croatia, Yugoslavia
D. Keglević ; Tracer Laboratory, Department of Organic Chemistry and Biochemistry, »Ruder Boskovic« Institute, POB' 1016, 41001, Zagreb, Croatia, Yugoslavia


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Abstract

Simultaneous and stepwise deprotection of the fully benzylated
a. and ~-n-glucopyranosyl esters of N-benzyloxycarbonyl- and N-
tert-butoxycarbonyl-0-benzyl-L-serine (I and V) was studied, and
a. and ~ anomers of 1-0-(L-seryl)-D-glucopyranose were isolated as
hygroscopic trifluoroacetate salts II o. and II ~ which were characterized
by subsequent conversion into the corresponding N-
acetyl- and -0-acetylated derivatives III and IV, respectively.
Catalytic hydrogenation of V ~ afforded 1-0-[N-(tert-butoxycarbonyl)-
L-seryl]-~-n-glucopyranose (VI ~), whereas the same treatment
of the a. anomer of V led to concomitant l -;.2 acyl migration
to give a mixture of VI a. and its 2-0-isomer VII, highly enriched
in the a. anomer. Acety'lation of the mixture yielded the peracetylated
1- and 2-0-acyl derivatives IX a. and XII a , also prepared by
definite methods. The 1H NMR spectra of a-n-anomers of 2,3,4,6-
-tetra-O-acetyl-1-0- and l ,3,4,6-tetra-O-acetyl-2-0-[N-(tert-butoxycarbonyl)- 0-(benzyl)-L-seryl] glucopyranoses (VIII a. and X a)
revealed that the seryl 0-benzyl substituent causes strong shielding
of the adjacent acetoxyl groups.

Keywords

Hrčak ID:

195856

URI

https://hrcak.srce.hr/195856

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