✦ LIBER ✦

Oxyhalogenation of glycals for the synthesis of anti-tumor-active 2′-halo daunorubicin analogs

✍ Scribed by Derek Horton; Waldemar Priebe

Book ID: 102641409
Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 451 KB
Volume: 136
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85212-5

No coin nor oath required. For personal study only.

✦ Synopsis

Alkoxyhalogenation of L-rhamnal diacetate with daunomycinone and Niodosuccinimide afforded 37% of 7-O-(3,4-di-0-acetyl-2,6-dideoxy-2-iodo-c+Lmannopyranosyl)daunomycinone (4, NSC 331,962) and 7% of the /3-L-gluco analog (NSC 353,457); a similar procedure with L-fucal diacetate gave 77% of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-Ziodo-a-L-talopyranosyl)daunomycinone (NSC 327,472). Compound 4 showed high activity (T/C 247) and low toxicity in the P-388 lymphocytic leukemia screen in mice.

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