(4S,5R)-5-methyltetrahydro-2,4-furandiol -Drug Synthesis Database

【结构式】

【分子编号】54262

【品名】(4S,5R)-5-methyltetrahydro-2,4-furandiol

【CA登记号】

【分子式】C₅H₁₀O₃

【分子量】118.1326

【元素组成】C 50.84% H 8.53% O 40.63%

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：(III)

The omega iodoalkyl thiazole intermediate (XII) is obtained as follows: The cyclization of 2-hydroxypropionaldehyde dimethyl acetal (I) with acetaldehyde (II) by means of warm Dowex (H+) and catalyzed by 2-deoxyribose-5-phosphate aldolase (DERA) gives the chiral tetrahydrofuran derivative (III), which is acylated with Ac-Cl and pyridine to yield the acetoxy compound (IV). The reaction of (IV) with BF3/Et2O, propane-1,3-dithiol (V) and TiCl4 affords the protected dithiane (VI), which is oxidized with oxalyl chloride in DMSO to provide the ketone (VII). The Wittig condensation of (VII) with phosphine oxide (VIII) by means of BuLi in THF provides the protected alkyl thiazole (IX), which is treated with HgClO4 to cleave the dithiane ring and yield carbaldehyde (X). Finally, this aldehyde is coupled with iodomethylenephosphorane (XI) by means of NaHMDS in THF/HMPA to afford the target omega iodoalkyl thiazole intermediate (XII).

参考文献中间体

合成目标

【1】 Wong, C.-H.; Liu, J.; Aldolase-catalyzed asymmetric synthesis of novel pyranose synthons as a new entry to heterocycles and epothilones. Angew Chem. Int Ed 2002, 41, 8, 1404.

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)	54261	1,1-dimethoxy-2-propanol	42919-42-6	C₅H₁₂O₃	详情	详情
(II)	11974	Acetaldehyde	75-07-0	C₂H₄O	详情	详情
(III)	54262	(4S,5R)-5-methyltetrahydro-2,4-furandiol		C₅H₁₀O₃	详情	详情
(IV)	54263	(2R,3S)-5-hydroxy-2-methyltetrahydro-3-furanyl acetate	n/a	C₇H₁₂O₄	详情	详情
(V)	29729	1,3-propanedithiol; 3-sulfanylpropylhydrosulfide	109-80-8	C₃H₈S₂	详情	详情
(VI)	54264	(1S,2R)-1-(1,3-dithian-2-ylmethyl)-2-hydroxypropyl acetate	n/a	C₁₀H₁₈O₃S₂	详情	详情
(VII)	54265	(1S)-1-(1,3-dithian-2-ylmethyl)-2-oxopropyl acetate		C₁₀H₁₆O₃S₂	详情	详情
(VIII)	47000	(2-methyl-1,3-thiazol-4-yl)methyl(diphenyl)phosphine oxide; 4-[(diphenylphosphoryl)methyl]-2-methyl-1,3-thiazole		C₁₇H₁₆NOPS	详情	详情
(IX)	54266	(1S,2E)-1-(1,3-dithian-2-ylmethyl)-2-methyl-3-(2-methyl-1,3-thiazol-4-yl)-2-propenyl acetate		C₁₅H₂₁NO₂S₃	详情	详情
(X)	44531	(1S,2E)-2-methyl-3-(2-methyl-1,3-thiazol-4-yl)-1-(2-oxoethyl)-2-propenyl acetate		C₁₂H₁₅NO₃S	详情	详情
(XI)	44532	(iodomethylene)(triphenyl)phosphorane		C₁₉H₁₆IP	详情	详情
(XII)	44493	(1S,3Z)-4-iodo-1-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl acetate		C₁₃H₁₆INO₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Wong, C.-H.; Liu, J.; Aldolase-catalyzed asymmetric synthesis of novel pyranose synthons as a new entry to heterocycles and epothilones. Angew Chem. Int Ed 2002, 41, 8, 1404.

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)	54261	1,1-dimethoxy-2-propanol	42919-42-6	C₅H₁₂O₃	详情	详情
(II)	11974	Acetaldehyde	75-07-0	C₂H₄O	详情	详情
(III)	54262	(4S,5R)-5-methyltetrahydro-2,4-furandiol		C₅H₁₀O₃	详情	详情
(IV)	54263	(2R,3S)-5-hydroxy-2-methyltetrahydro-3-furanyl acetate	n/a	C₇H₁₂O₄	详情	详情
(V)	29729	1,3-propanedithiol; 3-sulfanylpropylhydrosulfide	109-80-8	C₃H₈S₂	详情	详情
(VI)	54264	(1S,2R)-1-(1,3-dithian-2-ylmethyl)-2-hydroxypropyl acetate	n/a	C₁₀H₁₈O₃S₂	详情	详情
(VII)	54265	(1S)-1-(1,3-dithian-2-ylmethyl)-2-oxopropyl acetate		C₁₀H₁₆O₃S₂	详情	详情
(VIII)	47000	(2-methyl-1,3-thiazol-4-yl)methyl(diphenyl)phosphine oxide; 4-[(diphenylphosphoryl)methyl]-2-methyl-1,3-thiazole		C₁₇H₁₆NOPS	详情	详情
(IX)	54266	(1S,2E)-1-(1,3-dithian-2-ylmethyl)-2-methyl-3-(2-methyl-1,3-thiazol-4-yl)-2-propenyl acetate		C₁₅H₂₁NO₂S₃	详情	详情
(X)	44531	(1S,2E)-2-methyl-3-(2-methyl-1,3-thiazol-4-yl)-1-(2-oxoethyl)-2-propenyl acetate		C₁₂H₁₅NO₃S	详情	详情
(XI)	44532	(iodomethylene)(triphenyl)phosphorane		C₁₉H₁₆IP	详情	详情
(XII)	44493	(1S,3Z)-4-iodo-1-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-3-butenyl acetate		C₁₃H₁₆INO₂S	详情	详情

Extended Information