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【结 构 式】

【分子编号】38932

【品名】(1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,2-ethanediol

【CA登记号】

【 分 子 式 】C9H15N3O5

【 分 子 量 】245.23532

【元素组成】C 44.08% H 6.17% N 17.13% O 32.62%

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:(IV)

The reaction of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (I) with methanesulfonyl chloride and pyridine gives the mesylate (II), which by treatment with sodium azide in DMF is converted into 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (III). Selective hydrolysis of (III) with 1N HCl in ethanol affords 3-azido-3-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose (IV) (1), which is oxidized with sodium metaperiodate to the aldehyde (V). The reduction of (V) with NaBH4 in EtOH gives 3-azido-3-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose (VI), which is treated with tosyl chloride and pyridine to yield the corresponding 5-O-tosylate (VII) (2). The reaction of (VII) with potassium thiobenzoate (VIII) in hot DMF gives 3-azido-5-S-benzoyl-3-deoxy-1,2-O-isopropylidene-5-thio-alpha-D-xylofuranose (IX), which is treated successively with NaOMe in methanol, to induce cyclization, with refluxing HCl in methanol, to eliminate the isopropylidene group, and finally with acetic anhydride to furnish 1,2,4-tri-O-acetyl-3-azido-3-deoxy-5-thio-D-xylopyranose (X). The condensation of (X) with 4-nitrothiophenol (XI) by means of trimethylsilyl triflate in dichloromethane yields the corresponding acylated dithiopyranoside, which is finally deacetylated with sodium methoxide in methanol.

1 Meyer, W.; Synthese der 3-Amino-3-desoxy- und 3,6-Diamino-3,6-didesoxy-D-glucose. Chem Ber 1968, 101, 11, 3802-07.
2 Kuzuhara, H.; Ohrui, H.; Emoto, S.; Conversion of D-Glucose into d-Oxybiotin. Part I. Synthesis of 2,5-anhydro-3-azido-3-deoxy-D-xylose dimethyl acetal. Agr Biol Chem 1970, 34, 3, 375-380.
3 Kovácsné Bozó, E.; Kuszmann, J.; Szabó, G.; Boros, S.; Moravcsik, I. (Gedeon Richter Ltd.); Novel anticoagulant glycosides and pharmaceutical compsns. thereof. EP 0907656; WO 9749716 .
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) 29141 (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 582-52-5 C12H20O6 详情 详情
(II) 38930 (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydrofuro[2,3-d][1,3]dioxole C15H26O6S 详情 详情
(III) 38931 (3aR,5S,6S,6aR)-6-azido-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole; (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl azide C12H19N3O5 详情 详情
(IV) 38932 (1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,2-ethanediol C9H15N3O5 详情 详情
(V) 38933 (3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde C8H11N3O4 详情 详情
(VI) 38934 [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol C8H13N3O4 详情 详情
(VII) 38935 [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-methylbenzenesulfonate C15H19N3O6S 详情 详情
(VIII) 38936 potassium benzenecarbothioate C7H5KOS 详情 详情
(IX) 38937 S-[[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl] benzenecarbothioate C15H17N3O4S 详情 详情
(X) 38938 (2R,3R,4S,5S)-2,5-bis(acetoxy)-4-azidotetrahydro-2H-thiopyran-3-yl acetate C11H15N3O6S 详情 详情
(XI) 38898 4-nitrophenylhydrosulfide; 4-nitrobenzenethiol 1849-36-1 C6H5NO2S 详情 详情
(XII) 38939 (2S,3R,4S,5S)-5-(acetoxy)-4-azido-2-[(4-nitrophenyl)sulfanyl]tetrahydro-2H-thiopyran-3-yl acetate C15H16N4O6S2 详情 详情
Extended Information