143604-32-4Relevant academic research and scientific papers
Fluorination by anchimeric assistance of a diallylamino group: Application to the synthesis of some methyl aminofluoropentofuranosides
Giudicelli,Thome,Picq,Anker
, p. 19 - 37 (1993)
Methyl 2,3-trans-dialkylaminofluoro-α(or β)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino group assists the replacement of a trans- vicinal mesylate. Whatever the location of the dialkylamino group (α or β face of the ring), the regioselectivity of fluorination depends mainly on the α or β orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-β-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-α-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-β-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-α-D-arabinofuranoside. Attempts to obtain 2(or 3),5-difluoro analogues starting from corresponding dimesylates gave only disappointing results. Methyl 2,3-trans-dialkylaminofluoro-α(or B)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino group assists the replacement of a trans-vicinal mestylate. Whatever the location of the dialkylamino group (α or B face of the ring), the regioselectivity of fluorination depends mainly on the α or B orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-B-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-α-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-B-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-α-D-arabinofuranoside. Attempts to obtain 2(or 3), 5-difluoro analogues starting from corresponding dimesylates gave only disappointing results.
The synthesis and thermodynamic equilibrium of eight 5-O-benzyl-2 (or 3)-dimethylamino-3 (or 2)-o-mesyl-α (or β)-d-xylo (or arabino) methylfuranosides
Giudicelli,Thome,Picq,Anker
, p. 5123 - 5134 (2007/10/02)
Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (α and β) and 2 (α and β) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (α and β) in CD3CN
