[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl][(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]methanone -Drug Synthesis Database

【结构式】

【分子编号】45427

【品名】[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl][(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]methanone

【CA登记号】

【分子式】C₁₆H₁₇NO₃S

【分子量】303.38192

【元素组成】C 63.34% H 5.65% N 4.62% O 15.82% S 10.57%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XIX)

Alternatively, the (R,R)-5-(hydroxymethyl)-2-cyclopenten-1-ol (VII) can also be obtained as follows: The condensation of the chiral oxazolidinethione (XV) with the pentenoic anhydride (II) by means of n-BuLi in THF gives the N-pentenoyloxazolidinethione (XVI), which is condensed with crotonaldehyde (XVII) catalyzed by TiCl4 and (-)-spartein in dichloromethane, yielding the chiral adduct (XVIII). The ring-closing metathesis of (XVIII) by means of a Ru catalyst in dichloromethane affords the chiral cyclopentenol derivative (XIX), which is reduced to the target diol (VII) by means of LiBH4 in THF.

参考文献中间体

合成目标

【1】 Crimmins, M.T.; et al.; An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy. J Org Chem 2000, 65, 25, 8499.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	17666	1,1-dimethylpropionic 4-pentenoic anhydride		C₁₀H₁₆O₃	详情	详情
(VII)	17671	(1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol		C₆H₁₀O₂	详情	详情
(XV)	45425	(4S)-4-benzyl-1,3-oxazolidine-2-thione		C₁₀H₁₁NOS	详情	详情
(XVI)	41704	1-[(4R)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-4-penten-1-one		C₁₅H₁₇NO₂S	详情	详情
(XVII)	22517	(E)-2-butenal	4170-30-3	C₄H₆O	详情	详情
(XVIII)	45426	(2S,3R,4E)-2-allyl-1-[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-3-hydroxy-4-hexen-1-one		C₁₉H₂₃NO₃S	详情	详情
(XIX)	45427	[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl][(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]methanone		C₁₆H₁₇NO₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXIII)

Alternatively, 5(R)-(hydroxymethyl)-2-cyclopenten-1(R)-ol (VII) can also be obtained as follows: Acylation of the chiral oxazolidinethione (XIX) with the mixed anhydride (II) by means of BuLi in THF gives the N-pentenoyl-oxazolidinethione (XX), which by condensation with crotonaldehyde (XXI) catalyzed by TiCl4 and ()-spartein in dichloromethane yields the chiral adduct (XXII). The ring-closing metathesis of (XXII) by means of the ruthenium catalyst in dichloromethane affords the chiral cyclopentenol derivative (XXIII), which is reduced to the target diol (VII) by means of LiBH4 in THF.

参考文献中间体

合成目标

【1】 Crimmins, M.T.; et al.; An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy. J Org Chem 2000, 65, 25, 8499.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	17666	1,1-dimethylpropionic 4-pentenoic anhydride		C₁₀H₁₆O₃	详情	详情
(VII)	17671	(1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol		C₆H₁₀O₂	详情	详情
(XIX)	45425	(4S)-4-benzyl-1,3-oxazolidine-2-thione		C₁₀H₁₁NOS	详情	详情
(XX)	41704	1-[(4R)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-4-penten-1-one		C₁₅H₁₇NO₂S	详情	详情
(XXI)	22517	(E)-2-butenal	4170-30-3	C₄H₆O	详情	详情
(XXII)	45426	(2S,3R,4E)-2-allyl-1-[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-3-hydroxy-4-hexen-1-one		C₁₉H₂₃NO₃S	详情	详情
(XXIII)	45427	[(4S)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl][(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]methanone		C₁₆H₁₇NO₃S	详情	详情

Extended Information