Myoinsitol derivatives, process for preparing same, phosphorylat

Details Myoinsitol derivatives, process for preparing same, phosphorylat Myoinsitol derivatives, process for preparing same, phosphorylat

1991-02-20

1993-11-23

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

556443, 556449, 556482, 560106, 560182, 560198, 558122, C07F 708, C07F 718

Patent

active

052646050

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
The present invention relates to myoinositol derivatives having a probability that they will be used as medicines, a process for synthesizing the same, a novel phosphorylating agent represented by the formula (I) ##STR1## and its application.
2. Background Art
A simple process for the synthesis of myoinositol polyphosphoric acid has not been found. Furthermore, an easily usable phosphorylating agent for the hydroxyl groups of myoinositol has not been found.
In addition, a simple process for the synthesis of myoinositol polyphosphoric acid, an optical resolution of a myoinositol derivative and an advantageous process of an optical activator have not been found.


DISCLOSURE OF THE INVENTION

There are here disclosed a process for preparing a polyacylmyoinositol by reacting myoinositol with an acyl halide, a process for preparing a polyacylmyoinositol, a short process for easily preparing myoinositol polyphosphoric acid from a polyacylmyoinositol in a high yield, a process for preparing a polysilyl polyacylmyoinositol by reacting a polyacylmyoinositol with a silylating agent, a process for easily preparing myoinositol polyphosphoric acid in a high yield by reacting a polysilylmyoinositol or a polysilyl-polyacylmyoinositol with a phosphorylating agent, a process for preparing an optically active myoinositol polyphosphoric acid in accordance with these processes, an easy optical resolution of these products, and various intermediates in these processes.


BRIEF DESCRIPTION OF THE DRAWINGS

All of FIGS. 1 to 10 show synthetic processes of the present invention. Of these drawings, FIG. 5 shows the removal of benzoyl groups by the use of a Grignard reagent, FIG. 6 shows the synthesis of Ins(1,3,4,5)P.sub.4 and Ins(1,4,5)P.sub.3, FIG. 7 shows an asymmetric esterification of 1,3,5-tri-0-benzoyl-myoinositol, FIG. 8 shows the synthesis of optically active Ins(1,3,4,5)P.sub.4 and Ins-(1,4,5)P.sub.3, FIG. 9 shows the preparation of D-1,3,4,5-tetra-O-benzoyl-myoinositol by means of kinetic optical resolution, and FIG. 10 shows the removal of the benzoyl groups from 2,6-di-O-tert-butyldimethylsilyl-1,3,4,5-tetra-O-benzoylmyoinositol by the use of sodium methoxide.


BEST MODE FOR CARRYING OUT THE INVENTION

It is considered that when myoinositol is subjected to acylation, six hydroxyl groups are acylated substantially randomly However, it has been found that a 1,3,4,5-tetraacyl compound and a 1,3,5-triacyl compound can be produced in overwhelmingly large quantities under certain conditions. Furthermore, it has also been found that a 1,4,5-triacyl compound as well as other various polyacyl compounds can be obtained by changing the conditions. The utilization of these polyacylated myoinositols permits synthesizing myoinositol polyphosphoric acid.
Explanation will be made in reference to FIG. 1 as an example.
Myoinositol is reacted with an acyl halide in order to obtain a 1,3,5-triacyl compound 2 and a 1,3,4,5-tetraacyl compound 3. This 1,3,5-triacyl compound 2 is then reacted with R*X so as to introduce R* into the 4 position, thereby synthesizing a compound 4. Next, optical resolution is carried out, and the 2 and 4 positions of the compound are benzylated to obtain a compound 5. This compound 5 is then reacted with an alkali, so that the acyl groups at the 1, 3 and 5 positions of the compound 5 and the R* at the 4 position thereof are eliminated therefrom, in order to obtain a compound 7. On the other hand, reduction eliminable protective groups are introduced into the 2 and 6 positions of the 1,2,4,5-tetraacyl compound 3 in order to obtain a compound 6. This compound 6 is then reacted with a base to obtain a compound 7. This compound 7 is further reacted with a suitable phosphorylating agent, thereby obtaining a compound 8. Afterward, this compound 8 is subjected to catalytic reduction in order to obtain myoinositol 1,3,4,5-tetraphosphate 9.
On the other hand, suitable protective groups are introduced into the 2, 4 and 6 positions of the triacyl compound 2 to obtain a compound 10, and the

REFERENCES:
patent: 4801597 (1989-01-01), Stacpoole
patent: 4988682 (1991-01-01), Kozikowski
Journal of the Chemical Society, Chemical Communications, No. 8, 1989, pp. 482-483, Y. Watanabe et al.

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