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【结 构 式】

【分子编号】42089

【品名】(3R,4R,5R)-2-(acetoxy)-4-(benzoyloxy)-5-[1-(benzoyloxy)-2-propynyl]tetrahydro-3-furanyl benzoate

【CA登记号】

【 分 子 式 】C30H24O9

【 分 子 量 】528.51516

【元素组成】C 68.18% H 4.58% O 27.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

The reaction of the protected carbohydrate (I) with trimethylsilylacetylene (II) gives adduct (III) with no stereoselectivity at the reaction point. The oxidation of the OH group of (III) with DMP gives the corresponding oxo compound (IV), which is stereoselectively reduced with N-Selectride to yield the (R)-diastereomer (V) in a 33:1 ratio. The desilylation of (V) with TBAF in THF affords the free compound (VI), which is benzoylated with Bz2O, TEA and DMAP in acetonitrile to provide the tribenzoate (VII). The reaction of (VII) with Ac2O, H2SO4 and AcOH gives the 1-acetoxy compound (VIII), which is condensed with N6-benzoyladenine (IX) by means of Tms-OTf and TEA in acetonitrile, yielding the adenosine derivative (X). Finally, this compound is debenzoylated with ammonia in methanol.

1 Umino, T.; et al.; Nucleosides and nucleotides. Part 201: Alternative method to synthesize 9-(6,7-dideoxy-beta-D-allo-hept-5-ynofuranosyl)adenine, a selective and potent ligand for P-3 purinoceptor-like protein: A stereoselective reduction based on sugar puckering of the fu. Tetrahedron Lett 2000, 41, 33, 6419.
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) 42083 (2S,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furancarbaldehyde C18H38O5Si2 详情 详情
(II) 23897 ethynyl(trimethyl)silane;trimethylsilyl acetylene 1066-54-2 C5H10Si 详情 详情
(III) 42084 (1R)-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)-3-(trimethylsilyl)-2-propyn-1-ol C23H48O5Si3 详情 详情
(IV) 42085 1-((2S,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)-3-(trimethylsilyl)-2-propyn-1-one C23H46O5Si3 详情 详情
(V) 42086 1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)-3-(trimethylsilyl)-2-propyn-1-ol C23H48O5Si3 详情 详情
(VI) 42087 (2R,3S,4R,5R)-2-(1-hydroxy-2-propynyl)-5-methoxytetrahydro-3,4-furandiol C8H12O5 详情 详情
(VII) 42088 (2R,3R,4R,5R)-4-(benzoyloxy)-2-[1-(benzoyloxy)-2-propynyl]-5-methoxytetrahydro-3-furanyl benzoate C29H24O8 详情 详情
(VIII) 42089 (3R,4R,5R)-2-(acetoxy)-4-(benzoyloxy)-5-[1-(benzoyloxy)-2-propynyl]tetrahydro-3-furanyl benzoate C30H24O9 详情 详情
(IX) 10035 N-(9H-Purin-6-yl)benzamide; N6-Benzoyladenine 4005-49-6 C12H9N5O 详情 详情
(X) 42090 1-[(2R,3R,4R,5R)-5-[6-(benzoylamino)-9H-purin-9-yl]-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]-2-propynyl benzoate C40H29N5O8 详情 详情
Extended Information