Non-animal based lactose
View Patent ↗A synthetic procedure for the preparation of non-animal based lactose from 4′-epimeric analogue of lactose by use of orthogonal protecting groups, formation of a suitable leaving group at the 4′-position, stereochemical inversion by nucleophilic attack and deprotection.
1. A method for the synthesis of lactose from a 4′-epimeric analog of lactose by use of orthogonal protecting groups, formation of a suitable leaving group at the 4′-position, stereochemical inversion by nucleophilic attack and deprotection.
2. A method of synthesizing lactose, comprising the steps of:
a) protecting at least the 4′-epimeric functional group of a 4′-epimeric analog of lactose with a first protecting group;
b) protecting all other hydroxyl groups with a second protecting group;
c) removal of the first protecting group;
d) conversion of the 4′-epimeric functional group into a suitable leaving group;
e) nucleophilic attack leading to stereochemical inversion at the 4′-position; and
f) removal of the protecting groups;
and wherein the first and second protecting groups are orthogonal.
3. The method of claim 2 wherein, the first protecting group is an acetal or ketal.
4. The method of claim 2 wherein, the second protecting group is an ester.
5. The method of claim 2 wherein, the suitable leaving group is a mesylate or triflate.
6. The method of claim 2 wherein, the nucleophilic attack leads to formation of a stereochemically inverted ester.
7. The method of claim 2 wherein, the protecting groups are removed using a basic medium.
8. The method of claim 7 wherein; the basic medium comprises of sodium methoxide.