851367-08-3

Upstream product

• 108-24-7 acetic anhydride 
• 13039-64-0 (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol 
• 532-20-7 L-arabinose 

Downstream Products

• 13035-61-5 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose 
• 13035-61-5 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose 
• 1382683-49-9 2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine 

Relevant academic research and scientific papers

Formal total synthesis of α-elvucitabine

A formal total synthesis of α-elvucitabine has been achieved. The key intermediate 2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)- α-L-cytidine 1 has been prepared from inexpensive starting material L-arabinose in 29% overall yield.

Synthesis of a dimer of β-(1,4)-l-arabinosyl-(2 S,4 R)-4-hydroxyproline inspired by art v 1, the major allergen of mugwort

Nα-tert-Butoxycarbonyl-l-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-l-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.