Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. IV: Synthesis of enantiopure methyl (1S,2R,3R,4R,5S)-5-benzyloxycarbonylamino-2,3-isopropylidenedioxy-4-methoxycyclopentanecarboxylate

Add time:07/13/2019    Source:sciencedirect.com

The first total synthesis of a new enantiopure polyhydroxylated cyclopentyl β-amino acid [methyl (1S,2R,3S,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate] was achieved according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines. This approach is based on an intramolecular cyclization leading to 2-oxabicyclo[2.2.1]heptane derivatives. Epimerization of this amino acid derivative to methyl (1S,2R,3R,4R,5S)-2-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-4-methoxycyclopentanecarboxylate constitutes the first example of the preparation of one of the members of this family of amino acids with a stereochemistry that is not compatible with the above key cyclization step.

We also recommend Trading Suppliers and Manufacturers of METHYL 2-((BENZYLOXYCARBONYLAMINO)METHYL)-1H-IMIDAZOLE-5-CARBOXYLATE (cas 1070879-22-9). Pls Click Website Link as below: cas 1070879-22-9 suppliers

Prev:Tridiphane [2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane] an atrazine synergist: Enzymatic conversion to a potent glutathione S-transferase inhibitor
Next:Synthesis and enantiomeric excess determination of (6S)-1-(trimethylsilyloxy)-6-(N-methyl-N-benzyloxycarbonylamino)-cyclohexene)