(1R)-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)-3-(trimethylsilyl)-2-propyn-1-ol -Drug Synthesis Database

【结构式】

【分子编号】42084

【品名】(1R)-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)-3-(trimethylsilyl)-2-propyn-1-ol

【CA登记号】

【分子式】C₂₃H₄₈O₅Si₃

【分子量】488.88762

【元素组成】C 56.51% H 9.9% O 16.36% Si 17.23%

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：(III)

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.

参考文献中间体

合成目标

【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