(2R,3S,4S)-2-(hydroxymethyl)tetrahydro-3,4-furandiol -Drug Synthesis Database

【结构式】

【分子编号】46810

【品名】(2R,3S,4S)-2-(hydroxymethyl)tetrahydro-3,4-furandiol

【CA登记号】

【分子式】C₅H₁₀O₄

【分子量】134.132

【元素组成】C 44.77% H 7.51% O 47.71%

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：(I)

Demethylation of compound (XI) by means of BBr3 in refluxing dichloromethane gives 5-hydroxytetralinyl derivative (XII), which is then condensed with bromoacetic acid ethyl ester (XIII) by means of K2CO3 in DMF or acetonitrile to furnish (ethoxycarbonylmethoxy)tetraline derivative (XIV). Finally, the target product is obtained by saponification of the ethyl ester group of (XIV) by means of NaOH in 1,2-dimethoxyethane.

参考文献中间体

合成目标

【1】 Wenzel, T.; Nair, V.; Self-complementary oligodeoxyribonucleotides incorporating L-related isodeoxynucleosides: Synthesis, physical characterization, enzymology, and CD studies. Bioconjugate Chem 1998, 9, 6, 683.
【2】 Nair, V.; Taktakishvili, M.; Pommier, Y.; Neamati, N.; Recognition and inhibition of HIV integrase by a novel dinucleotide. Bioorg Med Chem Lett 2000, 10, 3, 249.

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)	46810	(2R,3S,4S)-2-(hydroxymethyl)tetrahydro-3,4-furandiol		C₅H₁₀O₄	详情	详情
(II)	46811	(2R,3S,4S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)tetrahydro-3,4-furandiol		C₂₁H₂₈O₄Si	详情	详情
(III)	46812	(2R,3R,4S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydro-3-furanol		C₂₄H₃₄O₄SSi	详情	详情
(IV)	46813	tert-butyl(diphenyl)silyl ((2R,3R,4S)-3-[[tert-butyl(diphenyl)silyl]oxy]-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydro-2-furanyl)methyl ether; tert-butyl[((2R,3R,4S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydro-3-furanyl)oxy]diphenylsilane		C₄₀H₅₂O₄SSi₂	详情	详情
(V)	10343	9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine	73-24-5	C₅H₅N₅	详情	详情
(VI)	46814	(2R,3S,4R)-4-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanol		C₁₀H₁₃N₅O₃	详情	详情
(VII)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(VIII)	46815	N-[9-[(3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl]-9H-purin-6-yl]benzamide		C₁₇H₁₇N₅O₄	详情	详情
(IX)	46816	N-[9-((3R,4S,5R)-5-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]-4-hydroxytetrahydro-3-furanyl)-9H-purin-6-yl]benzamide		C₃₈H₃₅N₅O₆	详情	详情
(X)	46817	sodium [((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)oxophosphoranolate		C₄₄H₃₈ClN₅NaO₉P	详情	详情
(XI)	46818	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-(hydroxymethyl)tetrahydro-3-furanyl acetate		C₁₈H₁₉N₃O₆	详情	详情
(XII)	46819	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate		C₆₂H₅₆ClN₈O₁₄P	详情	详情
(XIII)	46820	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[[(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-(hydroxymethyl)tetrahydro-3-furanyl]oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate		C₄₁H₃₈ClN₈O₁₂P	详情	详情
(XIV)	46821	cyanomethyl dihydrogen phosphate		C₂H₄NO₄P	详情	详情

Extended Information