N-benzyloxycarbonyl Group Research Articles

ChemInform Abstract: N‐Carboxylate Ion Equivalent. Part 2. Novel Transformations of N‐Benzyloxycarbonyl (Z) Group and N‐Allyloxycarbonyl Group into N‐tert‐Butyldimethylsilyloxycarbonyl Intermediate.

AbstractThe N‐benzyloxycarbonyl‐ and N‐allyloxycarbonylamino esters (I) are converted to the tert‐butyldimethylsiloxycarbonyl‐protected derivat‐ig ves (IV) by reaction with the silane (II) in the presence of Pd‐acetate (III).

Efficient removal of N-benzyloxycarbonyl group by a ‘push–pull’ mechanism using thioanisole–trifluoroacetic acid, exemplified by a synthesis of Met-enkephalin

The N-benzyloxycarbonyl group can be smoothly cleaved under mild conditions, using thioanisole–trifluoroacetic acid, which can deprotect O-benzyltyrosine without the formation of O-to-C rearrangement products; this deblocking method was successfully applied to the synthesis of Met-enkephalin.

Synthetic studies of Bacitracin. IV. Synthesis of unprotected thiazoline peptides.

Abstract For a total synthesis of bacitracian A, a synthetic method to secure unprotected thiazoline peptides must be established. 2-Aminomethyl-R-Δ2-thiazoline-4-carboxamide, 2-aminomethyl-R-Δ2-thiazoline-4-carboxylic acid, 2-aminomethyl-R-Δ2-thiazoline-4-carbonyl-l-leucine were synthesized by either the iminoether coupling method or by the dehydration method using N-benzyloxycarbonyl group and benzyl ester as protecting groups.

813. The kinetics and mechanism of the removal of the N-benzyloxycarbonyl group from N-benzyloxycarbonylglycine ethyl ester and related compounds in acetic acid containing hydrobromic acid or sulphuric acid

813. The kinetics and mechanism of the removal of the N-benzyloxycarbonyl group from N-benzyloxycarbonylglycine ethyl ester and related compounds in acetic acid containing hydrobromic acid or sulphuric acid

糖-アミノ酸結合体の研究 (第2報)

In order to synthesize the glycine ester of D-glucose, attempt was made to obtain the starting material, 6-O-(N-benzyloxycarbonylglycyl)-D-glucopyranose, by esterification of N-benzyloxycarbonylglycine with glucose derivative and it was found that dicyclohexylcarbodiimide is a good condensation agent. Compared to the ester condensation of N-benzyloxycabonylglycine and glucose derivative with mixed anhydride of other acids, the use of dicyclohexylcarbodiimide as the condensation agent was found to have the advantage of not forming a large amount of by-products. Further, the latter reagent was found to have entirely no effect on the urethan bond like N-benzyloxycarbonyl group. This process was used to obtain N-benzyloxycarbonylglycine ester of four kinds of glucose derivatives whose hydroxyls other than that at 6-position were protected, and three of them easily afforded 6-O-(N-benzyloxycarbonylglycyl)-α-D-glucopyranose.