(2R,3S,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-(phenylsulfanyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】41407

【品名】(2R,3S,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-(phenylsulfanyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl acetate

【CA登记号】

【分子式】C₂₁H₂₄Cl₃NO₉S

【分子量】572.847

【元素组成】C 44.03% H 4.22% Cl 18.57% N 2.45% O 25.14% S 5.6%

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：(I)

Phenylsulfanyl glycoside (I) was coupled with serine derivative (II) in the presence of N-bromosuccinimide, iodine and tetrabutylammonium triflate yielding the serine glycoside (III). Reductive cleavage of the trichloroethoxy carbonyl group of (III) with Zn and HOAc afforded amine (IV), which was acylated with (R)-3-(tetradecanoyloxy)tetradecanoic acid (V) using DCC and HOBt. Hydrogenolysis of the benzyl ester (VI) over palladium black provided carboxylic acid (VII).

参考文献中间体

合成目标

【1】 Ikeda, K.; et al.; Lipid A and related compounds. XXXVII. Determination of favorable binding linkages of lipid A analog to antigen moiety for synthetic vaccines. Chem Pharm Bull 2000, 48, 1, 32.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	41407	(2R,3S,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-(phenylsulfanyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl acetate	C₂₁H₂₄Cl₃NO₉S	详情	详情
(II)	41408	benzyl (2S)-3-hydroxy-2-(tetradecanoylamino)propanoate	C₂₄H₃₉NO₄	详情	详情
(III)	41409	benzyl (2S)-3-[((2R,3R,4R,5R,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-2-yl)oxy]-2-(tetradecanoylamino)propanoate	C₃₉H₅₇Cl₃N₂O₁₃	详情	详情
(IV)	41410	benzyl (2S)-3-([(2R,3R,4R,5R,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-3-aminotetrahydro-2H-pyran-2-yl]oxy)-2-(tetradecanoylamino)propanoate	C₃₆H₅₆N₂O₁₁	详情	详情
(V)	40612	(3R)-3-(tetradecanoyloxy)tetradecanoic acid	C₂₈H₅₄O₄	详情	详情
(VI)	41411	(1R)-1-[2-[((2R,3R,4R,5R,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-2-[[(2S)-3-(benzyloxy)-3-oxo-2-(tetradecanoylamino)propyl]oxy]tetrahydro-2H-pyran-3-yl)amino]-2-oxoethyl]dodecyl myristate	C₆₄H₁₀₈N₂O₁₄	详情	详情
(VII)	41412	(2S)-3-[((2R,3R,4R,5R,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-3-[[(3R)-3-(tetradecanoyloxy)tetradecanoyl]amino]tetrahydro-2H-pyran-2-yl)oxy]-2-(tetradecanoylamino)propionic acid	C₅₇H₁₀₂N₂O₁₄	详情	详情

Extended Information