-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】7-O-(4'-O-Acetyl-2',3',6'-trideoxy-3'-iodo-alpha-L-mannopyranosyl)daunomycinone

【CA登记号】

【分子式】C₂₉H₂₉IO₁₁

【分子量】680.45228

【开发单位】Servier (Originator)

【药理作用】Antibiotics and Alkaloids, Antineoplastic Antibiotics, ONCOLYTIC DRUGS, Anthracyclines

合成路线1

Reduction of ketone (I) with NaBH4 in MeOH at low temperature yielded alcohol (II) as the major product. This was treated with trifluoromethanesulfonic anhydride to provide triflate (III), which was displaced with NaI to form iodide (IV). Acetolysis of the methyl pyranoside (IV) produced the 1-alpha-O-acetyl derivative (V) along with minor amounts of the beta-anomer. The reaction of (V) with dry HCl in benzene gave the corresponding glycosyl chloride, which was subsequently coupled with daunorubicinone (VI) using HgO and HgBr2 to provide the title compound as the major anomer.

参考文献中间体

【1】 Pierre, A.; Aligiannis, N.; Skaltsounis, A.-L.; Marakos, P.; Leonce, S.; Atassi, G.; Pouli, N.; Mitaku, S.; Design, synthesis and biological activity of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo-hexopyranosyl)daunomycinone. Chem Pharm Bull 2000, 48, 1, 150.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	46981	(2S,3S,6R)-6-methoxy-2-methyl-4-oxotetrahydro-2H-pyran-3-yl acetate		C₉H₁₄O₅	详情	详情
(II)	46982	(2S,3R,4R,6R)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl acetate		C₉H₁₆O₅	详情	详情
(III)	46983	(2S,3S,4R,6R)-6-methoxy-2-methyl-4-[[(trifluoromethyl)sulfonyl]oxy]tetrahydro-2H-pyran-3-yl acetate		C₁₀H₁₅F₃O₇S	详情	详情
(IV)	46984	(2S,3S,4S,6R)-4-iodo-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl acetate		C₉H₁₅IO₄	详情	详情
(V)	46985	(2S,3S,4S,6S)-6-(acetoxy)-4-iodo-2-methyltetrahydro-2H-pyran-3-yl acetate		C₁₀H₁₅IO₅	详情	详情
(VI)	16223	(8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione	21794-55-8	C₂₁H₁₈O₈	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)