55085-33-1

Upstream product

• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 88238-35-1 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hexofuranose 
• 582-51-4 1,2-O-isopropylidene-α-D-allofuranose 
• 7022-86-8 1,2-O-isopropylidene-3,5,6-tri-O-p-tolylsulfonyl-α-D-allofuranose 
• 88238-34-0 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose 
• 55085-28-4 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 55085-29-5 3,6-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose 

Downstream Products

• 55085-34-2 homocytidine 
• 88238-38-4 1-(5-deoxy-β-D-arabino-hexofuranosyl)cytosine 

Relevant academic research and scientific papers

SYNTHESES OF 1-(5-DEOXY-Β-D-arabino-HEXOFURANOSYL)CYTOSINE

1-(5-Deoxy-β-D-arabino-hexofuranosyl)cytosine (4'-homoara-C) (11), a higher homolog of the antileukemic agent ara-C(1-β-D-arabinofuranosylcytosine), was prepared by two independent routes.The first one involved the inversion of configuration at C-2' of the D-ribo epimer (1-(5-deoxy-β-D-ribo-hexofuranosyl)cytosine, 4'-homocytidine) by the diphenylcarbonate technique; the 5-deoxy-D-ribo-hexofuranosyl moiety of 4'-homocytidine was obtained by way of an anti-Markovnikov addition of iodine trifluoroacetate to the double bond of 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose and reduction of the resulting iodide(s).In the second approach, 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-β-D-xylo-hexofuranose was acetolyzed and condensed with 4-acetyl-N-bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2',3'-anhydro intermediate.The structure of 11, in particular the configuration at C-2', was confirmed by its 1H- and 13C-n.m.r. spectra.