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Phthalimido-acetyl chloride

The total synthesis of nocardicin A and its analogues has received considerable attention. One of the first approaches 11,14) made use of the classical keten-imine reaction for construction of the P-lactam ring. Reaction of phthalimido-acetyl chloride with the thioimidate (13) in the presence of triethylamine gave the P-lactam (14). Removal of the sulphvu grouping and deprotection afforded 3-ANA, which could be acylated with the appropriate side-chain acid to give nocardicins D, E and G. Reaction of nocardicin D with hydroxylamine produced nocardicin A. Alternative routes 15,16) utilise triazines such as (15) to provide a source of the imines of type (16). This sequence also removes the necessity of a desulphurisation step. [Pg.6]

Synthesis of Derivatives of V-acetyllactosamine from Lactal Hexa-acetate. Hexa-0-acetyl-2-deoxy-2-phthalimido-/l-D-lactosyl Chloride, R. U. Lemieux, S. Z. Abbas, H. M. Burzynska, and R. M. Ratcliffe, Can. J. Chem., 60 (1982) 63-67. [Pg.25]

TeirorO-acetyl-D-glucopyranosyl bromide (Yield, %) Tri-0-acetyl-r>-rihofuranosyl chloride (Yield, %) Tri-O-benzoyl-o-ribofuranosyl chloride (Yield, %) Tri-O-benzoyl-o-xylofuranosyl chloride (Yield, %) S,B-Di-0-benzoylS-deoxy-S-phthalimido-B-ribofuranosyl chloride (Yield, %) ... [Pg.318]

The reaction of 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-D-glucopy-ranosyl chloride with the chloromercuri derivative of Ar ,iV -dimethyl-2-(methylthio)adenine, followed by desulfurization and de-O-acylation gave 9-(2-acetamido-2-deoxy-/3-D-glucosyl)-iV ,i -dimethyladenine (69)This... [Pg.325]

Acetyl-3,6-di-0-benzyl-2-deoxy-2-phthalimido- (-D-glucopyran-osyl chloride has been synthesised as outlined in Scheme 3 ... [Pg.83]

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See also in sourсe #XX -- [ Pg.5 ]



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