TY - JOUR
T1 - Synthesis and structure of d-glucuronolactone derived carboxamides
AU - Kandasamy, Saravanan
AU - Whitehead, George F.S.
AU - Vitórica-Yrezábal, Iñigo J.
AU - Gardiner, John M.
PY - 2023/2
Y1 - 2023/2
N2 - 5-O-Protected and 1,2-acetonide-protected D-glucurono-6,3-lactone furanosides were converted into novel furano-glucuronamides through treatment with ammonia. Several O3 protections and O5-deprotection routes afford new primary gluconamide derivatives. However, attempted O3-benzylations of O5-protected intermediates led instead to silyl migration (from O5-TDBMS), competitive N-benzylation or reclosure to the lactone are observed as competing processes. This is not seen the using 5-O-PMB protection which the provides the method of choice for obtaining a fully protection-differentiated glucofuranamide. X-ray crystal structures of a fully-protected glucurono-6,3-lactone lactone and a glucuronamide derivatives are reported.
AB - 5-O-Protected and 1,2-acetonide-protected D-glucurono-6,3-lactone furanosides were converted into novel furano-glucuronamides through treatment with ammonia. Several O3 protections and O5-deprotection routes afford new primary gluconamide derivatives. However, attempted O3-benzylations of O5-protected intermediates led instead to silyl migration (from O5-TDBMS), competitive N-benzylation or reclosure to the lactone are observed as competing processes. This is not seen the using 5-O-PMB protection which the provides the method of choice for obtaining a fully protection-differentiated glucofuranamide. X-ray crystal structures of a fully-protected glucurono-6,3-lactone lactone and a glucuronamide derivatives are reported.
UR - https://doi.org/10.1016/j.carres.2023.108744
U2 - 10.1016/j.carres.2023.108744
DO - 10.1016/j.carres.2023.108744
M3 - Article
SN - 0008-6215
SP - 108744
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -