1333041-95-4

Upstream product

• 1333041-93-2 (2R,3R,4S)-methyl 3-hydroxy-4-((2S,3S,6S)-6-((R)-1-hydroxypropan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methylpentanoate 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Stereodivergent synthesis of the C1-C9 tetrahydropyran subunit of zincophorin and isomers thereof

Zincophorin C1-C9 fragment and seven tetrahydropyran analogues were prepared diastereoselectively by sequential iodoetherification and radical hydrogen-transfer reactions. Stereoselective formation of 3,7-trans or 3,7-cis rings was rationalized through minimization of allylic-1,3 strain in chair-like transition states. Subsequent hydrogen-transfer provided 7,8-anti or 7,8-syn isomers under acyclic stereocontrol or endocyclic control respectively. The latter approach relies on the formation of a [4.4.0] bicyclic complexes resulting from the chelation of the oxygen of the tetrahydropyran ring and the ester by a bidentate Lewis acid. Georg Thieme Verlag Stuttgart New York.