2419-94-5Relevant articles and documents
Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties
Barbayianni, Efrosini,Fotakopoulou, Irene,Schmidt, Marlen,Constantinou-Kokotou, Violetta,Bornscheuer, Uwe T.,Kokotos, George
, p. 8730 - 8733 (2007/10/03)
Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.
Preferential hydrogenolysis of NAP esters provides a new orthogonal protecting group strategy for carboxylic acids
Gaunt, Matthew J.,Boschetti, Carlos E.,Yu, Jinquan,Spencer, Jonathan B.
, p. 1803 - 1806 (2007/10/03)
Selective hydrogenolysis of 2-naphthylmethyl (NAP) esters in the presence of a benzyl ester has been observed with a wide range of dicarboxylic acids. Orthogonal deprotection of NAP esters with challenging substrates can be achieved if the other carboxylic acids in the molecule are protected with 4-trifluoromethyl benzyl group instead of benzyl groups.
PROPERTIES OF Nα,Nca-DI-TERT-BUTYLOXYCARBONYL-ω-CARBAMOYL-α-AMINO ACIDS AND DIRECT SYNTHESIS OF PROTECTED HOMOGLUTAMIC ACID DERIVATIVES
Sakura, Naoki,Hirose, Kyoko,Hashimoto, Tadashi
, p. 3506 - 3509 (2007/10/02)
The protected carboxamide function of Nα,Nca-di-tert-butyloxy-carbonyl-ω-carbamoyl-α-amino acids worked well with nucleophilic reagents.Applying this novel reactivity, we developed an efficient synthetic route to Nα-tert-butyloxycarbonylhomoglutamic acid and its derivatives, including Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester, from Nα,Nca-di-tert-butyloxycarbonylhomoglutamine.KEYWORDS - protected homoglutamic acid synthesis; Nca-tert-butyloxycarbonylated carboxamide; hydrolysis; selective deprotection; Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester; Nα-tert-butyloxycarbonylhomoglutamic acid α-tert-butyl ester; Nα-tert-butyloxycarbonylhomoglutamine; optical purity