(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol -Drug Synthesis Database

【结构式】

【分子编号】34204

【品名】(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol

【CA登记号】

【分子式】C₂₉H₂₇N₅O₃

【分子量】493.56528

【元素组成】C 70.57% H 5.51% N 14.19% O 9.72%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

A new method for the synthesis of title compound has been reported: The reaction of 5'-O-triphenylmethyl-2'-deoxyadenosine (I) with CS2, methyl iodide and NaH gives the corresponding xanthate (II), which is reduced with tributyl hydrogen stannide to 5'-O-triphenylmethyl-2',3'-dideoxyadenosine (III). Finally, this compound is deprotected in the usual way.

参考文献中间体

合成目标

【1】 Samukov, V.V.; Ofitserov, V.I.; Synthesis od 2',3'-dideoxynucleosides. Bioorg Khim 1983, 9, 1, 52-59.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	34204	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol	C₂₉H₂₇N₅O₃	详情	详情
(II)	34205	O-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl] S-methyl carbonodithioate	C₃₁H₂₉N₅O₃S₂	详情	详情
(III)	34206	9-[(2R,5S)-5-[(trityloxy)methyl]tetrahydro-2-furanyl]-9H-purin-6-ylamine; 9-[(2R,5S)-5-[(trityloxy)methyl]tetrahydro-2-furanyl]-9H-purin-6-amine	C₂₉H₂₇N₅O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The elimination reaction of (III) with sodium ethoxide in DMF gives 2',3'-dideoxy-2',3'-didehydroadenosine (V), which is hydrogenated with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 McCarthy, J.R.; et al.; Purine nucleosides. XIV. Unsaturated furanosyl adenine nucleosides prepared via base-catalysed elimination reactions of 2'-deoxyadenosine derivatives. J Am Chem Soc 1966, 88, 7, 1549-53.
【2】 Castaner, J.; Hopkins, S.J.; Serradell, M.N.; Blancafort, P.; 2',3'-Dideoxyadenosine. Drugs Fut 1982, 7, 4, 244.

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)	34204	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol		C₂₉H₂₇N₅O₃	详情	详情
(II)	36381	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate		C₃₆H₃₃N₅O₅S	详情	详情
(III)	36382	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate		C₁₇H₁₉N₅O₅S	详情	详情
(V)	11994	[(2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol	7057-48-9	C₁₀H₁₁N₅O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

The reaction of 5'-triphenylmethyl-2'-deoxyadenosine (I) with p-toluenesulfonyl chloride in pyridine gives 5'-triphenylmethyl-3'-(p-toluenesulfonyl)-2'-deoxyadenosine (II), which by partial hydrolysis with acetic acid yields 3'-p-toluenesulfonyl)-2'-deoxyadenosine (III). The reaction of (III) with ethylmercaptane (A) by means of sodium ethoxide affords 3'-ethylthio-2',3'-dideoxyadenosine (IV), which is finally desulfurized by treatment with Raney-Ni in refluxing methyl cellosolve - ethanol (100 C).

参考文献中间体

合成目标

【1】 Robins, M.J.; et al.; The synthesis of 2',3'-dideoxyadenosine from 2'-deoxyadenosine. J Am Chem Soc 1964, 86, 17, 3585-86.
【2】 Robins, M.J.; et al.; Purine nucleosides. XII. The preparation of 2',3'-dideoxyadenosine, 2',5'dideoxyadenosine and 2',3',5'-trideoxyadenosine from 2'-deoxyadenosine. Biochem J 1966, 5, 1, 224-231.
【3】 Castaner, J.; Hopkins, S.J.; Serradell, M.N.; Blancafort, P.; 2',3'-Dideoxyadenosine. Drugs Fut 1982, 7, 4, 244.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	23712	1-ethanethiol; ethylhydrosulfide	75-08-1	C₂H₆S	详情	详情
(I)	34204	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol		C₂₉H₂₇N₅O₃	详情	详情
(II)	36381	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate		C₃₆H₃₃N₅O₅S	详情	详情
(III)	36382	(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate		C₁₇H₁₉N₅O₅S	详情	详情
(IV)	36383	[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3-(ethylsulfanyl)tetrahydro-2-furanyl]methanol		C₁₂H₁₇N₅O₂S	详情	详情

Extended Information