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【结 构 式】

【分子编号】41409

【品名】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

【CA登记号】

【 分 子 式 】C39H57Cl3N2O13

【 分 子 量 】868.24536

【元素组成】C 53.95% H 6.62% Cl 12.25% N 3.23% O 23.96%

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:(III)

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).

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 CAS号 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