SS-555, -Drug Synthesis Database

【结构式】

【药物名称】SS-555

【化学名称】6,6'-Di-O-octanoyl-alpha,alpha-trehalose
　　　　　　6-O-Octanoyl-alpha-D-glucopyranosyl alpha-D-glucopyranoside 6-octanoate

【CA登记号】84396-33-8

【分子式】C₂₈H₅₀O₁₃

【分子量】594.7029

【开发单位】Japan Tobacco (Originator), SSP (Originator)

【药理作用】Chemopreventive Agents, Oncolytic Drugs, AP-1 Inhibitors, TNF-alpha Release Inhibitors

合成路线1

2,2',3,3'-Tetra-O-benzyl-alpha,alpha-trehalose (III) was prepared by condensation of trehalose (I) with benzaldehyde, followed by alkylation of the resulting bisbenzylidene derivative (II) with benzyl chloride and then acid hydrolysis of the benzylidene ketal. Acylation of (III) with octanoyl chloride (IV) in the presence of pyridine provided diester (V). Finally, catalytic hydrogenolysis of the benzyl protecting groups yielded the title compound.

参考文献中间体

【1】 Fukushi, K. (SSP Co., Ltd.); Antitumor formulation containing lipopolysaccharide with trehalose derivs.. US 4612304 .
【2】 Kukita, K.; Shibata, A.; Katori, T.; Nishikawa, Y.; Yoshimoto, K. (SSP Co., Ltd.); alphaalpha-Trehalose-6,6'-middle chained aliphatic acid diester and a pharmaceutical agent containing the same. DE 3241199; FR 2534259; GB 2133399 .

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)	33680	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]tetrahydro-2H-pyran-3,4,5-triol		C₁₂H₂₂O₁₁	详情	详情
(II)	33681	(4aR,6R,7R,8R,8aS)-6-[[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol		C₂₆H₃₀O₁₁	详情	详情
(III)	33682	(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-6-[[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol		C₄₀H₄₆O₁₁	详情	详情
(IV)	11123	Octanoyl chloride; n-Caprylyl chloride;Capryloyl chloride	111-64-8	C₈H₁₅ClO	详情	详情
(V)	33683	[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-6-([(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-hydroxy-6-[(octanoyloxy)methyl]tetrahydro-2H-pyran-2-yl]oxy)-3-hydroxytetrahydro-2H-pyran-2-yl]methyl octanoate		C₅₆H₇₄O₁₃	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)