[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate -Drug Synthesis Database

【结构式】

【分子编号】11999

【品名】[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate

【CA登记号】

【分子式】C₁₁H₁₂N₂O₅

【分子量】252.22676

【元素组成】C 52.38% H 4.8% N 11.11% O 31.72%

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：(IV)

A new synthesis of 2',3'-dideoxyadenosine has been described: The reaction of uridine (I) with methyl orthoformate and p-toluenesulfonic acid gives the cyclic orthoester (II), which is acetylated with acetic anhydride at 100 C to the acetate (III). The reaction of (III) with acetic anhydride at temperatures over 120 C yields 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydrouridine (IV), which is hydrogenated to 5'-O-acetyl-2',3'-dideoxyuridine (V).

参考文献中间体

合成目标

【1】 Shiragami, H.; Shirae, H.; Irie, Y.; Yokozeki, K.; Yasuda, N.; The synthesis of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine. Nucl Acid Res Symp Ser 1988, 20, 20, 17-18.

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)	11996	1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine	58-96-8	C₉H₁₂N₂O₆	详情	详情
(I)	12001	1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione	5983-09-5	C₉H₁₂N₂O₄	详情	详情
(II)	11997	1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4(1H,3H)-pyrimidinedione		C₁₁H₁₄N₂O₇	详情	详情
(III)	11998	[(3aR,4R,6R,6aR)-6-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate		C₁₃H₁₆N₂O₈	详情	详情
(IV)	11999	[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate		C₁₁H₁₂N₂O₅	详情	详情
(V)	12000	[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl acetate		C₁₁H₁₄N₂O₅	详情	详情
(VI)	12001	1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione	5983-09-5	C₉H₁₂N₂O₄	详情	详情
(VII)	10343	9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine	73-24-5	C₅H₅N₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

2) The reaction of uridine (I) with methyl orthoformate and p-toluenesulfonic acid gives the cyclic orthoester (II), which is acetylated with acetic anhydride at 100 C, yielding the 5'-acetoxy derivative (III). The reaction of (III) with acetic anhydride at temperatures over 120 C affords 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydrouridine (IV), which is hydrogenated to 5'-O-acetyl-2',3'-dideoxyuridine (V). Hydrolysis of (V) affords 2',3'-dideoxyuridine (VI), which is finally submitted to a transdideoxyribosylation with hypoxanthine (VII) by incubation in an appropriate medium with Escherichia coli AJ 2595 resting cells.

参考文献中间体

合成目标

【1】 Shiragami, H.; Shirae, H.; Irie, Y.; Yokozeki, K.; Yasuda, N.; The synthesis of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine. Nucl Acid Res Symp Ser 1988, 20, 20, 17-18.
【2】 Shirae, H.; Kobayashi, K.; Shiragami, H.; Irie, Y.; Yasuda, N.; Yokozeki, K.; Production of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine from 2',3'-dideoxyuridine and the corresponding purine bases by resting cells of Escherichia coli AJ 2595. Appl Environ Microbiol 1989, 55, 2, 419-24.
【3】 Prous, J.; Castaner, J.; DIDEOXYINOSINE. Drugs Fut 1990, 15, 6, 569.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	60593	p-xylene		C₈H₁₀	详情	详情
(I)	11996	1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine	58-96-8	C₉H₁₂N₂O₆	详情	详情
(II)	11997	1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4(1H,3H)-pyrimidinedione		C₁₁H₁₄N₂O₇	详情	详情
(III)	11998	[(3aR,4R,6R,6aR)-6-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate		C₁₃H₁₆N₂O₈	详情	详情
(IV)	11999	[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate		C₁₁H₁₂N₂O₅	详情	详情
(V)	12000	[(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl acetate		C₁₁H₁₄N₂O₅	详情	详情
(VI)	12001	1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione	5983-09-5	C₉H₁₂N₂O₄	详情	详情
(VII)	12794	9H-Purin-6-ol; Hypoxanthine	68-94-0	C₅H₄N₄O	详情	详情

Extended Information