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Thyromimetics IV. Synthesis of some derivatives of 3,3′,5-triiodo-D and L-thyronine

✍ Scribed by Benjamin Blank

Publisher
John Wiley and Sons
Year
1964
Tongue
English
Weight
461 KB
Volume
53
Category
Article
ISSN
0022-3549

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✦ Synopsis

Synthesis of Some Derivatives of 3,3', 5-Triiodo-~ and L-Thytonine By BENJAMIN BLANK Three pathways leading t o the methyl ethers of 3,3',5-triiodo-D and Gthyronine were explored. In these syntheses the acetyl, benzoyl, and trifluoroacetyl grou s were studied as suitable amine-protecting groups, thus providing a number of Eitherto unreported thyronine derivatives. Consideration of the over-all yields and the quality of the products from the various reaction sequences showed that the acetyl group was best suited for the protection of the amino group in these syntheses.

URING A STUDY in which the thyromimetic activities of several ethers of thyromimetic substances were determined (1) it became desirable to prepare the methyl ethers of 3,3',5-triiodo-D and L-thyronine (VII-D and L). The synthesis of the L-isomer has been described b y Tomita el al.

(2). The other reports dealing with VII-L contained biological data only (3, 4).

In the synthesis reported b y Tomita et al.

(2), 3,3',5-triiodo-~-thyronine methyl ester (IIu-L) was treated with diazomethane to give the methyl ether of IIu-L. Basic hydrolysis followed b y neutralization yielded VII-L in about 43% overall yield.

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