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Synthesis of I-125 labeled photoaffinity rapamycin analogs

✍ Scribed by Arthur Y. L. Shu; Dennis S. Yamashita; Dennis A. Holt; J. Richard Heys

Publisher
John Wiley and Sons
Year
1996
Tongue
French
Weight
520 KB
Volume
38
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two no-carrier-added 125I-labeled photoaffinity raparnycin analogs were prepared: 7-demethoxy-7-(4-azido-3-~~~l-benzyloxy)rapamycin (2) and its C28-C29 seco analog 3 . The key reactions of the synthesis were substitution of the C7 methoxyl of rapamycin (1) with 4-azido-3-tributylstannylbenzyloxy group, exchange of tributyltin with 1251 using Na125l and Chloramine-T, and a ZnCI2 mediated retro-Aldol cleavage of the c 2 8 -c 2 9 bond of rapamycin.

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