PHOSPHONIC ACIDS ANALOGUES OF GLYCEROL 3-PHOSPHATE.
Item
-
Title
-
PHOSPHONIC ACIDS ANALOGUES OF GLYCEROL 3-PHOSPHATE.
-
Identifier
-
AAI8312356
-
identifier
-
8312356
-
Creator
-
LALINDE, NHORA P.
-
Contributor
-
Robert Engel
-
Date
-
1983
-
Language
-
English
-
Publisher
-
City University of New York.
-
Subject
-
Chemistry, Organic
-
Abstract
-
The main focus of this thesis was the preparation of Phosphonic acids analogues of glycerol 3-phosphate, which included nitrogen, epoxy and hydroxyl analogues.;Glycerol 3-phosphate is at a branch point between lipid metabolism and glycolysis; the important role that this material plays in metabolism suggests that it is quite a reasonable target for antimetabolic activity by structurally related phosphonic acids.;For the preparation of the hydroxyl analogue, namely 1,3,4-trihydroxybutylphosphonic acid, advantage was taken of the fact that addition of organoboranes to an unsymmetrical olefin proceeds to place the boron atom on the less substituted of the two carbons forming a double bond. Hydroboration provided a simple, convenient synthetic route for the anti-Markovnikov hydration of Diisopropyl (S)-(E)-3,4-diisopropylidine-3,4-dihydroxybutene-1-yl phosphonate.;The preparation of the nitrogen analogue N-(2,3-dihydroxypropyl) phosphoramide was accomplished by the Gabriel synthesis of primary amines. This method offers the advantage of the absence of secondary or tertiary amine contamination of the primary amine, the toleration of a wide range of other functional groups in the molecule and the mild conditions needed for accomplishing both stages: condensation and hydrolysis.;Many attempts for the preparation of 1,2-epoxy-3,4-dihydroxybutane phosphonic acid were made; they included the treatment of halohydrins with base, the direct epoxidation of the vinyl phosphonate by m-chloroperbenzoic acid, and a synthesis similar to the one reported by Glamkowsky et al. for fosfomycin using sodium tungstate as catalyst. All of these efforts were without great success.
-
Type
-
dissertation
-
Source
-
PQT Legacy CUNY.xlsx
-
degree
-
Ph.D.
-
Program
-
Chemistry
