Four-component-condensation of D-isoserine or L-isoserine, diphenylmethyl isocyanide and p-(benzyloxy)benzaldehyde was used to construct a functionalized β-lactam ring system which was transformed in 4 steps into 3-aminocardicinic acid. A protected side c
Isenring,Hofheinz
p. 2591 - 2597
(2007/10/02)
Process for 4-(D-3-amino-3-carboxypropoxy)-phenylglyoxylic acid oxime derivatives
Process for 4-(D-3-amino-3-carboxypropoxy)phenylglyoxylic acid oxime as an amino-protected ester comprising alkylating an amino-protected D-methionine silyl ester with an alkyl or benzyl iodide; cyclizing the alkylsulfonium iodide to an amino-protected D-homoserine lactone; hydrolyzing the lactone to an amino-protected D-homoserine in aqueous base; coupling, to form an ether, the amino-protected D-homoserine as an ester with an ester of 4-hydroxyphenylglyoxylic acid; and forming the oxime of the ether or alternatively coupling the D-homoserine ester with a protected-oxime of an esterified 4-hydroxyphenylglyoxylic acid. The product is useful in preparing the antibiotic FR 1923.
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(2008/06/13)
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