462099-69-0

Upstream product

• 462099-62-3 (S)-5-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-bis-triethylsilanyloxy-propyl]-dihydro-furan-2-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 462099-63-4 (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((S)-5-oxo-tetrahydro-furan-2-yl)-2-triethylsilanyloxy-propionaldehyde 
• 384341-88-2 (S)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-dihydro-furan-2-one 

Relevant academic research and scientific papers

Synthesis of a small repertoire of non-racemic 5a-carbahexopyranoses and 1-thio-5a-carbahexopyranoses

A short and practical entry to optically pure 5a-carbahexopyranose and 1-thio-5a-carbahexopyranose representatives is described. Besides a few functional group and protecting group manipulations, the synthetic scheme counts on two fundamental carbon-carbon bond-forming reactions, namely (i) a regio- and stereoselective aldol addition between heterocyclic (silyloxy)diene donors (6 or 13) and D-glyceraldehyde as the acceptor (7) and (ii) a chemo- and stereoselective silylative cycloaldolization involving bifunctional aldehydes (10, 16, and 21). The 1H NMR based configurational and conformational assignment of target structures 1-5 and bicyclic intermediates 11, 12, 17, 18, and 22 is discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.