(1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】26517

【品名】(1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate

【CA登记号】

【分子式】C₅₂H₆₁N₃O₁₀

【分子量】888.07056

【元素组成】C 70.33% H 6.92% N 4.73% O 18.02%

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：(XIII)

Protection of the 4- and 6-hydroxyl groups of (XI) was achieved by conversion into the benzylidene acetal (XII) upon treatment with benzaldehyde and formic acid. The remaining 2- and 3-hydroxyl groups of (XII) were benzoylated with benzoyl chloride to afford the corresponding benzoate ester (XIII). After reduction of the azide group of (XIII) to amine (XIV) with H2S and pyridine, condensation with hexadecanoyl chloride produced the corresponding amide (XV). Deprotection of the acetal group of (XV) with TFA in CH2Cl2 gave diol (XVI), which was finally treated with SO3-Me3N complex, and then with NaHCO3 to form the title disulfate sodium salt.

参考文献中间体

合成目标

【1】 Banville, J.; Martel, A.; Aruffo, A.A. (Bristol-Myers Squibb Co.); Sulfated beta-glycolipid derivs. as cell adhesion inhibitors. EP 0671406; JP 1995285985; US 5565433 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
	16480	Palmitoyl Chloride; hexadecanoyl chloride	112-67-4	C₁₆H₃₁ClO	详情	详情
(XI)	26515	(1R,2Z)-1-((1S)-1-azido-2-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]ethyl)-2-hexadecenyl benzoate		C₃₁H₄₉N₃O₈	详情	详情
(XII)	26516	(1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8R,8aR)-7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate		C₃₈H₅₃N₃O₈	详情	详情
(XIII)	26517	(1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate		C₅₂H₆₁N₃O₁₀	详情	详情
(XIV)	26518	(1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-aminoethyl)-2-hexadecenyl benzoate		C₅₂H₆₃NO₁₀	详情	详情
(XV)	26519	(1R,2Z)-1-[(1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-(palmitoylamino)ethyl]-2-hexadecenyl benzoate		C₆₈H₉₃NO₁₁	详情	详情
(XVI)	26520	(1R,2Z)-1-[(1S)-2-[[(2S,3R,4S,5S,6R)-3,4-bis(benzoyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-1-(palmitoylamino)ethyl]-2-hexadecenyl benzoate		C₆₁H₈₉NO₁₁	详情	详情

Extended Information