528566-63-4

Upstream product

• 528566-59-8 6-nitro-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 528566-62-3 3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone 
• 121195-24-2 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 1137111-80-8 methyl (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylate 
• 528566-64-5 [((1S,4S,5S,6R,7R)-6,7-Bis-benzyloxy-3-oxo-2-oxa-bicyclo[2.2.1]hept-5-ylcarbamoyl)-methyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part VI: Synthesis and incorporation of the novel polyhydroxylated 5-aminocyclopent-1-enecarboxylic acids into peptides

The first total synthesis of enantiopure methyl (3aR,4S,5S,6R,6aS)-4- benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3] dioxole-5-carboxylate has been carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines. This approach is based on an intramolecular cyclization that leads to 2-oxabicyclo[2.2.1]heptane derivatives. E1cb elimination of the methoxy substituent was observed when attempting to incorporate these β-amino acid into peptides. As a result, the synthesis and incorporation of the first polyhydroxylated 5-aminocyclopent-1-enecarboxylic acid into peptides were developed.

Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate

The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on

Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes: Incorporation of polyhydroxylated carbocyclic β-amino acids into peptides

(Matrix presented) A promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first