167901-80-6

Upstream product

• 190188-86-4 Toluene-4-sulfonic acid (2R,3S,6R)-3-benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-ylmethyl ester 
• 1730-25-2 allylmagnesium bromide 
• 190188-69-3 Toluene-4-sulfonic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 107108-67-8 tert-butyl 2,3-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 190188-73-9 (2R,3S,6R)-3-Benzyloxy-2-((S)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 
• 190188-72-8 (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 
• 500733-68-6 (S)-4-Benzyloxy-4-[(2R,5R)-5-((R)-1-iodo-butyl)-tetrahydro-furan-2-yl]-butan-1-ol 
• 500733-66-4 (S)-4-Benzyloxy-4-((2R,5R)-5-iodomethyl-tetrahydro-furan-2-yl)-butan-1-ol 
• 167901-90-8 tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside 
• 167901-86-2 tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8Z-enopyranoside 

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.