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

Autor:	Rosalino Balo, Pablo Thomas, Miguel Alegre, Juan C. Estevez, Raquel G. Soengas, Amalia M. Estévez, Ramón J. Estévez
Rok vydání:	2014
Předmět:	Inorganic Chemistry Heptane chemistry.chemical_compound Transformation (genetics) Enantiopure drug Stereochemistry Chemistry Intramolecular force Organic Chemistry Physical and Theoretical Chemistry Alkylation Catalysis
Zdroj:	Tetrahedron: Asymmetry. 25:583-590
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2014.03.005
Popis:	Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzyl-3,6-deoxy-6-nitro-β-d-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-α-d-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzyl-5-deoxy-5-nitromethyl-β-d-xylofuranoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-α-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-benzyloxy-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- dihydroxycyclopentanecarboxylate and this novel β-amino acid was incorporated into peptides. © 2014 Elsevier Ltd. All rights reserved.
Databáze:	OpenAIRE
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