Synthesis of C-glycoside analogues of alpha -galactosylceramide (KRN7000) and its derivatives.
Item
-
Title
-
Synthesis of C-glycoside analogues of alpha -galactosylceramide (KRN7000) and its derivatives.
-
Identifier
-
AAI3287105
-
identifier
-
3287105
-
Creator
-
Pu, Jun.
-
Contributor
-
Adviser: Richard W. Franck
-
Date
-
2006
-
Language
-
English
-
Publisher
-
City University of New York.
-
Subject
-
Chemistry, Organic
-
Abstract
-
The C-glycoside analogue of alpha-galactosylceramide(KRN7000) 4 was first synthesized by Dr.Yang in Professor Richard W. Franck's lab at Hunter College in 2001. The C-glycoside is a powerful immunostimulant and shows better anti malaria and anti cancer activities than its O-glycoside counterpart, KRN7000.;We had tried several novel synthetic methods to get this important compound. The successful synthesis method was a linear route (20 steps, 5% overall yield), which was based on Wittig-Sharpless asymmetric epoxidation (SAE) reactions. This approach is a very powerful tool to construct optically active epoxides with high yield and high ee. A variety of C-glycoside analogues could be made by using two different Sharpless chiral auxiliaries. The target C-glycoside 4 and several C-glycosides derivatives were made and SAR experiments could be carried through. An unusual Lewis acid promoted neighboring group participation double SN2 opening of the epoxides mechanism was proposed to explain the retention of the 3-N stereocenter during the Ti(O-i-Pr)2(N3)2 opening of the epoxide.
-
Type
-
dissertation
-
Source
-
PQT Legacy CUNY.xlsx
-
degree
-
Ph.D.
