benzyl (2R,3R,4S,5R,6R)-3,5-bis(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-4-yl ether; (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran -Drug Synthesis Database

【结构式】

【分子编号】52053

【品名】benzyl (2R,3R,4S,5R,6R)-3,5-bis(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-4-yl ether; (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran

【CA登记号】

【分子式】C₃₅H₃₈O₅S

【分子量】570.74972

【元素组成】C 73.65% H 6.71% O 14.02% S 5.62%

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：(IX)

Condensation of galactose pentaacetate (I) with 2-[2-(2-chloroethoxy)ethoxy]ethanol (II) in the presence of boron trifluoride etherate afforded the galactopyranoside (III). Subsequent hydrolysis of the acetate esters of (III) to give (IV) was carried out employing K2CO3 in MeOH. The galactose 3-hydroxyl group of (IV) was selectively protected as the p-methoxybenzyl ether (VI) by treatment with p-methoxybenzyl chloride (V) in the presence of dibutyltin oxide. After acetylation of the remaining free hydroxyl groups of (VII) to give (VIII), oxidative cleavage of its p-methoxybenzyl ether by means of cerium ammonium nitrate afforded the 2,4,6-triacetylated pyranoside (VIII). This was condensed with the galactose thioglycoside (IX) in the presence of methyl triflate to furnish the protected disaccharide (X). The benzyl protecting groups of (X) were then removed by hydrogenolysis yielding (XI).

参考文献中间体

合成目标

【1】 Yu, L.; Jack, R.M.; Jones, D. (La Jolla Pharmaceutical Co.); Conjugates comprising galactose alpha 1,3 galactosyl epitopes and methods of using same. EP 1137652; WO 0034296 .
【2】 Jones, D.S.; Engle, S.B.; Yu, L.; Jack, R.M. (La Jolla Pharmaceutical Co.); Methods and formulations for reducing circulating antibodies. WO 0033887 .

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)	52047	[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(acetoxy)tetrahydro-2H-pyran-2-yl]methyl acetate		C₁₆H₂₂O₁₁	详情	详情
(II)	14748	2-[2-(2-Chloroethoxy)ethoxy]-1-ethanol; 2-(2-(2-Chloroethoxy)ethoxy)ethanol	5197-62-6	C₆H₁₃ClO₃	详情	详情
(III)	52048	(2R,3S,4S,5R,6S)-3,5-bis(acetoxy)-2-[(acetoxy)methyl]-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]tetrahydro-2H-pyran-4-yl acetate		C₂₀H₃₁ClO₁₂	详情	详情
(IV)	52049	(2S,3R,4S,5R,6R)-2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol		C₁₂H₂₃ClO₈	详情	详情
(V)	11910	4-Methoxybenzyl chloride; 1-(Chloromethyl)-4-methoxybenzene; alpha-Chloro-4-methoxytoluene; 4-(Chloromethyl)phenyl methyl ether	824-94-2	C₈H₉ClO	详情	详情
(VI)	52050	(2S,3R,4S,5R,6R)-2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-6-(hydroxymethyl)-4-[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3,5-diol		C₂₀H₃₁ClO₉	详情	详情
(VII)	52051	(2R,3R,4S,5R,6S)-5-(acetoxy)-2-[(acetoxy)methyl]-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-4-[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl acetate		C₂₆H₃₇ClO₁₂	详情	详情
(VIII)	52052	(2R,3R,4S,5R,6S)-5-(acetoxy)-2-[(acetoxy)methyl]-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-4-hydroxytetrahydro-2H-pyran-3-yl acetate		C₁₈H₂₉ClO₁₁	详情	详情
(IX)	52053	benzyl (2R,3R,4S,5R,6R)-3,5-bis(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-4-yl ether; (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(methylsulfanyl)tetrahydro-2H-pyran		C₃₅H₃₈O₅S	详情	详情
(X)	52054	(2R,3S,4S,5R,6S)-5-(acetoxy)-2-[(acetoxy)methyl]-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-4-([(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]oxy)tetrahydro-2H-pyran-3-yl acetate		C₅₂H₆₃ClO₁₆	详情	详情
(XI)	52055	(2R,3S,4S,5R,6S)-5-(acetoxy)-2-[(acetoxy)methyl]-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-4-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]tetrahydro-2H-pyran-3-yl acetate		C₂₄H₃₉ClO₁₆	详情	详情

Extended Information