TY - JOUR
T1 - A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside
AU - Deal, S. Todd
AU - Horton, Derek
PY - 1999/1/31
Y1 - 1999/1/31
N2 - The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.
AB - The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.
KW - 2,6-Dideoxy-2-fluoro-L-talose
KW - Anthracycline glycons
KW - Configurational inversion
KW - Fluoro sugars
UR - http://www.scopus.com/inward/record.url?scp=0032971878&partnerID=8YFLogxK
U2 - 10.1016/S0008-6215(98)00325-5
DO - 10.1016/S0008-6215(98)00325-5
M3 - Article
AN - SCOPUS:0032971878
SN - 0008-6215
VL - 315
SP - 187
EP - 191
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1-2
ER -