300693-11-2

Upstream product

• 300693-05-4 (2'S,3'S) ethyl 2-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-6-O-trityl-β-D-glucopyranoside 
• 197644-79-4 (2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 30571-51-8 5,6-dideoxy-1,2-O-isopropylidene-α-D-allo-hex-5-endofuranoside 
• 300693-10-1 (2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-6-O-trityl-α-D-glucopyranosyl)-5,6-dideoxy-1,2-O-isopropylidene-α-D-allo-hex-5-endofuranoside 

Relevant academic research and scientific papers

Synthesis and biological evaluation of cyclophostin: A 5',6-tethered analog of adenophostin A

The synthesis, conformational analysis and biological evaluation of 5'-6-tethered adenophostin A, so-called cyclophostin 14, and its de-adeninylated analog 15 are described. They are prepared via ring-closing metathesis of diolefin 28, consecutive coupling of the central building block 33 to 6-N-benzoyladenine or propargyl alcohol, respectively, followed by phosphorylation and deprotection. NMR spectroscopy and a molecular dynamics simulation indicated that the 5'-6-tether induces a conformational change from 2'-endolsyn in 1 to 3'-endo/anti in 14. The unexpected small loss of Ca2+-releasing potency of cyclophostin 14, which is reflected by the low EC50/IC50 ratio in comparison with cycloribophostin 15, suggests that the interaction of the adenine with IP3R plays a decisive role in determining the high activity of adenophostin A (1). (C) 2000 Elsevier Science Ltd.