TY - JOUR
T1 - Oxyhalogenation of glycals for the synthesis of anti-tumor-active 2′-halo daunorubicin analogs
AU - Horton, Derek
AU - Priebe, Waldemar
PY - 1985/2/28
Y1 - 1985/2/28
N2 - Alkoxyhalogenation of l-rhamnal diacetate with daunomycinone and N-iodosuccinimide afforded 37% of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-l-mannopyranosyl)daunomycinone (4, NSC 331,962) and 7% of the β-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-2-iodo-α-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.
AB - Alkoxyhalogenation of l-rhamnal diacetate with daunomycinone and N-iodosuccinimide afforded 37% of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-l-mannopyranosyl)daunomycinone (4, NSC 331,962) and 7% of the β-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-2-iodo-α-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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U2 - 10.1016/0008-6215(85)85212-5
DO - 10.1016/0008-6215(85)85212-5
M3 - Article
C2 - 4005892
AN - SCOPUS:0022433573
SN - 0008-6215
VL - 136
SP - 391
EP - 396
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -