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【结 构 式】

【分子编号】33050

【品名】[(2R,3S)-3-hydroxytetrahydro-2-furanyl]methyl trifluoromethanesulfonate

【CA登记号】

【 分 子 式 】C6H9F3O5S

【 分 子 量 】250.1956696

【元素组成】C 28.8% H 3.63% F 22.78% O 31.97% S 12.82%

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:(XVI)

In an alternative procedure, deoxyribose (XIV) was reduced to 2-deoxy-D-erythropentitol (XV) with NaBH4. Acid-catalyzed cyclization of (XV) produced (IX), which was converted to triflate (XVI) using trifluoromethanesulfonic anhydride and pyridine. Displacement with tetrabutylammonium azide provided azido derivative (XVII). Further treatment with trifluoromethanesulfonic anhydride gave triflate (XVIII), which was then displaced with potassium thioacetate to yield thioester (XII). This was hydrolyzed with NaOMe as above to furnish thiol (XIII).

1 Lin, Y.-I.; Bitha, P.; Sakya, S.; Strohmeyer, T.W.; Bush, K. (American Cyanamid Co.); Novel 2-thiosubstd. carbapenems. CA 2118961; EP 0617036; JP 1994321948; US 5602118 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 33043 (2R,3S)-2-(hydroxymethyl)tetrahydro-3-furanol C5H10O3 详情 详情
(XII) 33046 S-[(2R,3R)-2-(azidomethyl)tetrahydro-3-furanyl] ethanethioate C7H11N3O2S 详情 详情
(XIII) 33047 (2R,3R)-2-(azidomethyl)tetrahydro-3-furanthiol; (2R,3R)-2-(azidomethyl)tetrahydro-3-furanylhydrosulfide C5H9N3OS 详情 详情
(XIV) 33048 (3S,4R)-3,4,5-trihydroxypentanal 18546-37-7 C5H10O4 详情 详情
(XV) 33049 (2R,3S)-1,2,3,5-pentanetetrol C5H12O4 详情 详情
(XVI) 33050 [(2R,3S)-3-hydroxytetrahydro-2-furanyl]methyl trifluoromethanesulfonate C6H9F3O5S 详情 详情
(XVII) 33051 (2R,3S)-2-(azidomethyl)tetrahydro-3-furanol C5H9N3O2 详情 详情
(XVIII) 33052 (2R,3S)-2-(azidomethyl)tetrahydro-3-furanyl trifluoromethanesulfonate C6H8F3N3O4S 详情 详情
Extended Information