(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】48969

【品名】(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate

【CA登记号】

【分子式】C₁₄H₁₈O₆

【分子量】282.29332

【元素组成】C 59.57% H 6.43% O 34.01%

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：(VI)

Synthesis of intermediate monosaccharide (VI): The reaction of L-arabinose (I) with benzyl alcohol and HCl (gas) gives 1-O-benzyl-L-arabinose (II), which is treated with 2,2-dimethoxypropane (III) and TsOH to yield the 3,4-O-isopropylidene derivative (IV). The selective acetylation of (IV) with Ac2O and pyridine affords the 2-O-acetyl derivative (V), which is finally treated with HOAc in hot water to provide the intermediate 2-O-acetyl-1-O-benzyl-L-arabinose (VI).

参考文献中间体

合成目标

【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202.

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)	17520	(3R,4S,5S)tetrahydro-2H-pyran-2,3,4,5-tetrol; L-(+)-Arabinose	7296-56-2	C₅H₁₀O₅	详情	详情
(II)	48966	2-Benzyloxytetrahydropyran-3,4,5-triol		C₁₂H₁₆O₅	详情	详情
(III)	10722	1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane	77-76-9	C₅H₁₂O₂	详情	详情
(IV)	48967	(3aS,6S,7R,7aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol		C₁₅H₂₀O₅	详情	详情
(V)	48968	(3aS,6S,7R,7aS)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate		C₁₇H₂₂O₆	详情	详情
(VI)	48969	(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate		C₁₄H₁₈O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Synthesis of intermediate disaccharide (XVII): The regioselective glycosylation of intermediate arabinose derivative (VI) with the intermediate acetimidate (XIII) by means of BF3/Et2O gives the disaccharide (XIV), which is silylated with Tes-OTf and lutidine in dichloromethane to yield the fully protected disaccharide (XV). Elimination of the benzyl protecting group of (XV) by hydrogenation with H2 over Pd/C in hot ethyl acetate affords the hemiacetal (XVI), which is converted into the target trichloroacetimidate (XVII) by reaction with trichloroacetonitrile and DBU in dichloromethane.

参考文献中间体

合成目标

【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	48969	(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate	C₁₄H₁₈O₆	详情	详情
(XIII)	48975	(3R,4R,5R)-2-[(2,2,2-trichloroethanimidoyl)oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₂₇H₄₄Cl₃NO₇Si₂	详情	详情
(XIV)	48976	(2S,3R,4R,5R)-2-[[(2S,3R,4S,5S)-3-(acetoxy)-2-(benzyloxy)-5-hydroxytetrahydro-2H-pyran-4-yl]oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₃₉H₆₀O₁₂Si₂	详情	详情
(XV)	48977	(2S,3R,4R,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(benzyloxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₄₅H₇₄O₁₂Si₃	详情	详情
(XVI)	48978	(2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-hydroxy-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₃₈H₆₈O₁₂Si₃	详情	详情
(XVII)	48979	(2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₄₀H₆₈Cl₃NO₁₂Si₃	详情	详情

Extended Information