(2R,3R,4R,5S)-4,5-bis(acetoxy)-2-methyltetrahydro-3-furanyl acetate -Drug Synthesis Database

【结构式】

【分子编号】16748

【品名】(2R,3R,4R,5S)-4,5-bis(acetoxy)-2-methyltetrahydro-3-furanyl acetate

【CA登记号】62211-93-2

【分子式】C₁₁H₁₆O₇

【分子量】260.24384

【元素组成】C 50.77% H 6.2% O 43.03%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The condensation of bis(trimethylsilyl)fluorouracil (I) with 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose (II) in the presence of trimethylsilyl trifluoromethanesulfonate (III) gives the fully protected compound (IV), which is finally deprotected by the usual methods.

参考文献中间体

合成目标

【1】 D'Souza, R.; Arnold, W.; Van Koeveringe, J.A.; Kiss, J.; Stereospecific synthesis of the anticancer agent 5'-deoxy-5-fluorouridine (5-DFUR) and its 5'-deuterated derivatives. Helv Chim Acta 1982, 65, 5, 1522.

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)	30002	5-fluoro-1,3-bis(trimethylsilyl)-2,4(1H,3H)-pyrimidinedione		C₁₀H₁₉FN₂O₂Si₂	详情	详情
(II)	16748	(2R,3R,4R,5S)-4,5-bis(acetoxy)-2-methyltetrahydro-3-furanyl acetate	62211-93-2	C₁₁H₁₆O₇	详情	详情
(III)	30003	trifluoromethyl (trimethylsilyl)methyl sulfone; trimethyl[[(trifluoromethyl)sulfonyl]methyl]silane		C₅H₁₁F₃O₂SSi	详情	详情
(IV)	30004	(2R,3R,4R,5R)-4-(acetoxy)-2-[5-fluoro-2,4-dioxo-3-(trimethylsilyl)-3,4-dihydro-1(2H)-pyrimidinyl]-5-methyltetrahydro-3-furanyl acetate		C₁₆H₂₃FN₂O₇Si	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The acetylation of 5'-deoxy-5-fluorocytidine (I) with acetic anhydride in dry pyridine gives 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine (II), which is condensed with pentyl chloroformate (III) by means of pyridine in dichromethane yielding 2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine (IV). Finally, this compound is deacetylated with NaOH in dichloromethane/water. The diacetylated cytidine (II) can also be obtained by condensation of 5-fluorocytosine (V) with 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose (VI) by means of trimethylchlorosilane in acetonitrile or HMDS and SnCl4 in dichloromethane..

参考文献中间体

合成目标

【1】 Hoshi, A.; Castañer, J.; Capecitabine. Drugs Fut 1996, 21, 4, 358.
【2】 Arasaki, M.; Ishitsuka, H.; Kurama, I.; Miwa, M.; Murasaki, C.; Shimma, N.; Umeda, I. (F. Hoffmann-La Roche AG); N-Oxycarbonyl substd. 5'-deoxy-5-fluorocytidines. EP 0602454; JP 1994211891; US 5472949 .
【3】 Arasaki, M.; Shimma, N.; Umeda, I.; et al.; The design and synthesis of a new tumor-selective fluoropyrimidine carbamate, capecitabine. Bioorg Med Chem Lett 2000, 8, 7, 1697.

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)	13569	4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydro-2-furanyl]-5-fluoro-2(1H)-pyrimidinone		C₉H₁₂FN₃O₄	详情	详情
(II)	16744	(2R,3R,4R,5R)-4-(acetoxy)-2-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-5-methyltetrahydro-3-furanyl acetate	161599-46-8	C₁₃H₁₆FN₃O₆	详情	详情
(III)	16745	1-[(chlorocarbonyl)oxy]pentane	638-41-5	C₆H₁₁ClO₂	详情	详情
(IV)	16746	(2R,3R,4R,5R)-4-(acetoxy)-2-[5-fluoro-2-oxo-4-[[(pentyloxy)carbonyl]amino]-1(2H)-pyrimidinyl]-5-methyltetrahydro-3-furanyl acetate	162204-20-8	C₁₉H₂₆FN₃O₈	详情	详情
(V)	16747	4-amino-5-fluoro-2(1H)-pyrimidinone; 5-fluorocytosine	2022-85-7	C₄H₄FN₃O	详情	详情
(VI)	16748	(2R,3R,4R,5S)-4,5-bis(acetoxy)-2-methyltetrahydro-3-furanyl acetate	62211-93-2	C₁₁H₁₆O₇	详情	详情

Extended Information