Synthetic heparin monosaccharides

1. A monosaccharide of General Formula X

in which the ring is of the D-Gluco stereochemistry;

wherein

X 1 is selected from the group consisting of alpha or beta thiomethyl or thiocresyl or trichloroacetimidoyl or t-butyldiphenylsilyloxy, alpha methoxy;

R H1 is selected from the group consisting of benzyl or substituted benzyl protecting group or R H1 and R A can combine together to form a cyclic carbamate;

R A is selected from the group consisting of an azido function, an NH-Dde, NH-DTPM;

or R H1 and R A can combine together to form a cyclic carbamate;

R S1 is selected from the group consisting of 4-methoxyphenyl; 4-methoxybenzyl, benzoyl, and 4-chlorobenzoyl;

R L is selected from a hydrogen atom or a levulinoyl.

2. The monosaccharide of claim 1 ,

wherein:

R A is azido or R A and R H1 combine to form a cyclic carbamate.

3. The monosaccharide of claim 1 , wherein R H1 is benzyl.

4. A monosaccharide of General Formula XIII,

in which the ring is of the D-Gluco stereochemistry;

wherein:

R S3 is selected from the group consisting of 4-methoxyphenyl; 4-methoxybenzyl, benzoyl, 4-chlorobenzoyl, allyloxycarbonyl and allyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, benzoyl, 4-chlorobenzoyl, and allyl, or R S4 and R B may be combined to form a cyclic carbamate;

R B is selected from the group consisting of an azido function and an amine, or R S4 and R B can combine together to form a cyclic carbamate;

R L is selected from the group consisting of a a hydrogen atom and a levulinoyl group;

X 3 is selected from the group consisting of a thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and tert-butyldiphenylsilyloxy; and the stereochemistry may be alpha or beta.

5. A monosaccharide of General Formula XVI,

wherein:

X 1 is selected from the group consisting of thiomethyl, thiocresyl, trichloroacetimidoyl, and a tbutyldiphenylsilyloxy; and the stereochemistry may be alpha or beta;

R L is selected from the group consisting of a hydrogen atom, a levulinoyl;

R S6 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl; benzoyl, 4-chlorobenzoyl, and tert-Butyldiphenylsilyl.

6. The monosaccharide of claim 1 , wherein the monosaccharide is of the formula:

7. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

8. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

9. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

10. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

11. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

12. The monosaccharide of claim 4 , wherein the monosaccharide is of the formula:

13. A monosaccharide of the formula: