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【结 构 式】

【分子编号】49120

【品名】2-azido-1,3-propanediol

【CA登记号】

【 分 子 式 】C3H7N3O2

【 分 子 量 】117.1076

【元素组成】C 30.77% H 6.02% N 35.88% O 27.32%

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)

2-Amino-1,3-propanediol (I) was reacted with in situ generated trifluoromethanesulfonyl azide, and the resulting 2-azido compound was purified by chromatography after conversion to the diacetate ester (II). Deacetylation of (II) with sodium methoxide gave 2-azido-1,3-propanediol (III), which was condensed with tosylate (IV) in the presence of NaH to produce the dihydroxyether (V). The primary alcohol group of (V) was then protected as the mono-silyl derivative (VI) employing tert-butyldiphenylsilyl chloride. After acylation of the free hydroxyl group of (VI) with the unsaturated acid (VII), the resulting ester (VIII) was desilylated by using HF in acetonitrile to yield alcohol (IX). The phosphorylating reagent (XII) was prepared by treatment of allyl phosphorodiamidite (X) with N-Boc-ethanolamine (XI). Phosphitylation of alcohol (IX) with phosphoramidite (XII), followed by oxidation of the intermediate phosphite ester with oxone , furnished phosphate (XIII). The azido group of (XIII) was then reduced to the corresponding amine (XIV) by employing (PhS)2Sn.

1 Rossignol, D.P.; Ishizaka, S.T.; Nault, A.; Lewis, M.; Rose, J.; McGuiness, P.; Hawkins, L.D. (Eisai Co., Ltd.); Immunological adjuvant cpd.. EP 1147117; US 6290973; WO 0044758 .
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) 23333 2-amino-1,3-propanediol; serinol 534-03-2 C3H9NO2 详情 详情
(II) 49119 3-(acetoxy)-2-azidopropyl acetate C7H11N3O4 详情 详情
(III) 49120 2-azido-1,3-propanediol C3H7N3O2 详情 详情
(IV) 49121 (3R)-3-hydroxydecyl 4-methylbenzenesulfonate C17H28O4S 详情 详情
(V) 49122 (3R)-1-(2-azido-3-hydroxypropoxy)-3-decanol C13H27N3O3 详情 详情
(VI) 49123 (3R)-1-(2-azido-3-[[tert-butyl(diphenyl)silyl]oxy]propoxy)-3-decanol C29H45N3O3Si 详情 详情
(VII) 49124 (Z)-5-dodecenoic acid C12H22O2 详情 详情
(VIII) 49125 (1R)-1-[2-(2-azido-3-[[tert-butyl(diphenyl)silyl]oxy]propoxy)ethyl]octyl (Z)-5-dodecenoate C41H65N3O4Si 详情 详情
(IX) 49126 (1R)-1-[2-(2-azido-3-hydroxypropoxy)ethyl]octyl (Z)-5-dodecenoate C25H47N3O4 详情 详情
(X) 49127   C15H33N2OP 详情 详情
(XI) 32500 tert-butyl 2-hydroxyethylcarbamate 26690-80-2 C7H15NO3 详情 详情
(XII) 49128   C16H33N2O4P 详情 详情
(XIII) 49129 (1R)-9-(allyloxy)-6-azido-1-heptyl-16,16-dimethyl-9,14-dioxo-4,8,10,15-tetraoxa-13-aza-9lambda(5)-phosphaheptadec-1-yl (Z)-5-dodecenoate C35H65N4O9P 详情 详情
(XIV) 49130 (1R)-9-(allyloxy)-6-amino-1-heptyl-16,16-dimethyl-9,14-dioxo-4,8,10,15-tetraoxa-13-aza-9lambda(5)-phosphaheptadec-1-yl (Z)-5-dodecenoate C35H67N2O9P 详情 详情
Extended Information