(3R)-3-hydroxydihydro-2(3H)-furanone -Drug Synthesis Database

【结构式】

【分子编号】64294

【品名】(3R)-3-hydroxydihydro-2(3H)-furanone

【CA登记号】

【分子式】C₄H₆O₃

【分子量】102.08984

【元素组成】C 47.06% H 5.92% O 47.02%

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)

Mitsunobu coupling of alcohol (I) with thioacetic acid affords the thioacetate ester (II), which is further hydrolyzed to thiol (III) by means of hydrazine hydrate in cold THF. Treatment of (R)-alpha-hydroxy-gamma-butyrolactone (IV) with methanesulfonyl chloride and Et3N provides the chiral mesylate (V). This is then condensed with thiol (III) in the presence of K2CO3 in DMF to furnish the title compound. (2)

参考文献中间体

合成目标

【1】 Angell, R.M.; Biggadike, K.; Farrell, R.M.; Flack, S.S.; Hancock, A.P.; Irving, W.R.; Lynn, S.M.; Procopiou, P.A.; Novel glucocorticoid antedrugs possessing a 21-(gamma-lactone) ring. J Chem Soc - Perkins Trans I 2002, 6, 831.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	47572	(4aS,4bR,5S,6aS,6bS,8R,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a-dimethyl-8-propyl-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one	C₂₅H₃₄F₂O₆	详情	详情
(II)	64292	S-{2-[(4aS,4bR,5S,6aS,8R,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-8-propyl-2,3,4,4a,4b,5,6,6a,9a,10,10a,10b,11,12-tetradecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6-yl]-2-oxoethyl} ethanethioate	C₂₇H₃₆F₂O₆S	详情	详情
(III)	64293	(4aS,4bR,5S,6aS,6bS,8R,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-8-propyl-6b-(2-sulfanylacetyl)-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one	C₂₅H₃₄F₂O₅S	详情	详情
(IV)	64294	(3R)-3-hydroxydihydro-2(3H)-furanone	C₄H₆O₃	详情	详情
(V)	64295	(3R)-2-oxotetrahydro-3-furanyl methanesulfonate	C₅H₈O₅S	详情	详情

Extended Information