Published in
Elsevier, Tetrahedron: Asymmetry, 6-7(25), p. 583-590
DOI: 10.1016/j.tetasy.2014.03.005
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Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes. Part 6. Synthesis and Incorporation into Peptides of the First Reported 2,3-Dihydroxycyclopentanecarboxylic Acid
,
Pablo Thomas,
Miguel Alegre,
Rosalino Balo,
Juan Carlos Estévez,
Ramón J. Estévez
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Abstract
a b s t r a c t Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzyl-3,6-deoxy-6-nitro-b-D-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-a-D-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzyl-5-deoxy-5-nitromethyl-b-D-xylo-furanoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-a-D-xylofuranoside were cyclized to (1R,3R, 4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane and (1R,3S,4S,5R,7R)-7-benzyl-oxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane, respectively. These 2-oxabicyclo[2.2.1]heptane derivatives were eventually transformed into enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-2,3-dihydr-oxycyclopentanecarboxylate and this novel b-amino acid was incorporated into peptides.