N-{(2S,3R,4R,5S,6R)-4-(allyloxy)-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide -Drug Synthesis Database

【结构式】

【分子编号】56359

【品名】N-{(2S,3R,4R,5S,6R)-4-(allyloxy)-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide

【CA登记号】

【分子式】C₃₁H₄₂N₂O₁₀

【分子量】602.68196

【元素组成】C 61.78% H 7.02% N 4.65% O 26.55%

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：(XLII)

Condensation of the glucopyranosyl chloride (XXXIX) with the protected glucosamine (XL) in the presence of silver triflate-s-collidine complex gave disaccharide (XLI). Subsequent dephthaloylation and ester hydrolysis of (XLI) by means of n-butylamine in boiling MeOH furnished (XLII). Chemoselective acylation of the amino group of (XLII) with Ac2O in MeOH provided acetamide (XLIII). The free hydroxyl groups of (XLIII) were then protected as the corresponding benzyl ethers (XLIV) employing benzyl bromide in the presence of barium oxide and barium hydroxyde. The O-allyl group of (XLIV) was then isomerized in the presence of DABCO and rhodium catalyst to the 1-propenyl analogue (XLV), which was further hydrolyzed to alcohol (XLVI) by treatment with HgCl2.

参考文献中间体

合成目标

【1】 Durette, P.L.; et al.; Synthesis of O-(2-acetamido-2-deoxy-beta-D-glucosyl)-(1--4)-N-acetylmuramoyl-L-alanyl-D-isoglutamine, the repeating disaccharide-dipeptide unit of the bacterial cell-wall peptidoglycan. Carbohydr Res 1979, 77, C1.
【2】 Durette, P.L.; Shen, T.-Y. (Merck & Co., Inc.); Immunologically active peptidyl disaccharides, methods of preparation and vaccine. EP 0018901 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXXIX)	56356	(2R,3S,4R,5R,6S)-3-(acetyloxy)-2-[(acetyloxy)methyl]-6-chloro-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)tetrahydro-2H-pyran-4-yl acetate	C₂₀H₂₀ClNO₉	详情	详情
(XL)	56357	N-{(2S,3R,4R,5S,6R)-4-(allyloxy)-2-(benzyloxy)-6-[(benzyloxy)methyl]-5-hydroxytetrahydro-2H-pyran-3-yl}acetamide	C₂₅H₃₁NO₆	详情	详情
(XLI)	56358	(2R,3R,4R,5R,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-4-(allyloxy)-6-(benzyloxy)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}oxy)-5-(acetyloxy)-6-[(acetyloxy)methyl]-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)tetrahydro-2H-pyran-4-yl acetate	C₄₅H₅₀N₂O₁₅	详情	详情
(XLII)	56359	N-{(2S,3R,4R,5S,6R)-4-(allyloxy)-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide	C₃₁H₄₂N₂O₁₀	详情	详情
(XLIII)	56360	N-[(2S,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-4-(allyloxy)-6-(benzyloxy)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide	C₃₃H₄₄N₂O₁₁	详情	详情
(XLIV)	56361	N-{(2S,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-4-(allyloxy)-6-(benzyloxy)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}oxy)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide	C₅₄H₆₂N₂O₁₁	详情	详情
(XLV)	56362	N-{(2S,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-1-propenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide	C₅₄H₆₂N₂O₁₁	详情	详情
(XLVI)	56363	N-{(2S,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-hydroxytetrahydro-2H-pyran-3-yl}oxy)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-3-yl}acetamide	C₅₁H₅₈N₂O₁₁	详情	详情

Extended Information