[(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl]methyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】56341

【品名】[(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl]methyl benzoate

【CA登记号】

【分子式】C₃₁H₃₉NO₈

【分子量】553.6526

【元素组成】C 67.25% H 7.1% N 2.53% O 23.12%

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：(XXIII)

In an alternative route, 2-N-acetyl-4,6-O-isopropylidene-D-glucosamine benzyl pyranoside (XVII) was alkylated with 1-bromo-2-butene (XVIII) in the presence of barium oxide and barium hydroxide to produce the 3-O-crotyl ether (XIX). After acidic hydrolysis of the isopropylidene ketal (XIX), the resultant diol (XX) was selectively mono-acylated at the primary hydroxyl with benzoyl chloride (XXI) to afford the 6-benzoate ester (XXII). Protection of the 3-hydroxyl group of (XXII) by means of dihydropyran (DHP) and p-toluenesulfonic acid gave rise to the tetrahydropyranyl ether (XXIII). After methanolysis of the benzoate ester of (XXIII) in the presence of NaOMe, the resultant primary alcohol (XXIV) was protected as the benzyl ether (XXV). Subsequent hydrolysis of the tetrahydropyranyl group of (XXV) in aqueous HOAc furnished the protected glucosamine intermediate (XXVI).

参考文献中间体

合成目标

【1】 Kiso, M.; et al.; A general, convenient synthesis of the repeating, disaccharide-dipeptide unit of the bacterial, cell-wall peptidoglycan by the oxazoline method. Carbohydr Res 1980, 83, 1, C8.
【2】 Kiso, M.; et al.; Synthesis and immunoadjuvant activities of the repeating, disaccharide-dipeptide unit of the bacterial, cell-wall peptidoglycan and of some carbohydrate analogs. Carbohydr Res 1982, 104, 2, 253.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVII)	56337	N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide		C₁₈H₂₅NO₆	详情	详情
(XVIII)	35252	(E)-1-bromo-2-butene	29576-14-5	C₄H₇Br	详情	详情
(XIX)	56338	N-{(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-[(E)-2-butenyloxy]-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl}acetamide		C₂₂H₃₁NO₆	详情	详情
(XX)	56339	N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4-[(E)-2-butenyloxy]-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide		C₁₉H₂₇NO₆	详情	详情
(XXI)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(XXII)	56340	{(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-hydroxytetrahydro-2H-pyran-2-yl}methyl benzoate		C₂₆H₃₁NO₇	详情	详情
(XXIII)	56341	[(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl]methyl benzoate		C₃₁H₃₉NO₈	详情	详情
(XXIV)	56342	N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4-[(E)-2-butenyloxy]-6-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl]acetamide		C₂₄H₃₅NO₇	详情	详情
(XXV)	56343	N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl]acetamide		C₃₁H₄₁NO₇	详情	详情
(XXVI)	56344	N-{(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]-5-hydroxytetrahydro-2H-pyran-3-yl}acetamide		C₂₆H₃₃NO₆	详情	详情

Extended Information