1401709-29-2

Upstream product

• 153097-69-9 allyl 2,3,6 tri-O-benzyl-α-D-glucopyranoside 
• 167646-21-1 allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside 

Downstream Products

• 1401709-30-5 prop-1-en-1-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside 
• 1401709-31-6 prop-1-en-1-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside 
• 1401709-32-7 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-D-galactopyranose 
• 1401709-33-8 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-D-galactopyranose 

Relevant academic research and scientific papers

Rearrangement reactions in the fluorination of D-glucopyranoside at?the C-4 position by DAST

Attempts to synthesize 4-deoxy-4-fluoro-KRN-7000 (2), a potential immune adjuvant, by fluorination of 4-hydroxy of α-D-glucopyranoside using DAST, were not successful. Instead, the unusual 5-deoxy-5-fluoro β-L-altrofurnoside and the corresponding 4-deoxy-4-fluoro α-D-glucopyranoside with retained configuration were obtained. In the presence of polar solvents, the reaction afforded the epoxide product, suggesting the bicyclic oxiranium ion intermediate to be involved in this reaction. Compound 2 was eventually achieved by treating 4-methanesufonated glucopyranoside with fluoride ion and found to be a weak agonist for CD1d and NKT cell activation.

Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal

Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-α-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl- D-galactal and allyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies.