190188-73-9

Upstream product

• 190188-86-4 Toluene-4-sulfonic acid (2R,3S,6R)-3-benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-ylmethyl ester 
• 190188-69-3 Toluene-4-sulfonic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 167901-80-6 tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside 
• 107108-67-8 tert-butyl 2,3-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 190188-71-7 (S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol 

Relevant academic research and scientific papers

C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-,1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyl-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs. the non-pyranoside substrates, but the selectivity in both cases was low.