20590-57-2

Upstream product

• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 76-83-5 trityl chloride 
• 20590-53-8 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 
• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 

Downstream Products

• 67950-19-0 1,2-O-isopropylidene-3-O-bis(2,2,2-trichloroethoxy)phosphoryl-5-O-trityl-α-D-ribofuranose 
• 226256-00-4 3-S-(benzothiazol-2-yl)-1,2-O-isopropylidene-3-thio-5-O-trityl-α-D-xylofuranose 
• 55735-86-9 3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 1037290-53-1 (E)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-ribo-hept-2-enitol 
• 70798-12-8 1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside 
• 145741-63-5 (+)-(2E)-Ethyl 3-<(2'R,3'R,4'R,5'R)-3'-benzyloxy-4',5'-isopropylidenedioxytetrahydrofuran-2'-yl>prop-2-enoate 

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.

The convergent synthesis and anticancer activity of broussonetinines related analogues

The convergent synthesis of broussonetinines related congeners 3 and 4 with the simple C13 alkyl side chain and differently configured pyrrolidine skeleton has been achieved. Our approach relied on the [3,3]-sigmatropic rearrangements of chiral allylic substrates derived from D-xylose. Cross metathesis of the common oxazolidinone intermediates 7 and 8 with tridec-1-ene followed by alkylative cyclization completed the construction of both C-alkyl iminosugars. The targeted compounds 3 and 4 were screened for antiproliferative/cytotoxic activities against multiple cancer cell lines by MTT assay. Compound 3 exhibited very good in vitro potency on Caco-2 and Jurkat cell lines with IC50 value of 5.1 μM and 5.8 μM, respectively.