(2S)-2-(acetamido)-3-methyl-3-sulfanylbutyric acid -Drug Synthesis Database

【结构式】

【分子编号】27255

【品名】(2S)-2-(acetamido)-3-methyl-3-sulfanylbutyric acid

【CA登记号】59-53-0

【分子式】C₇H₁₃NO₃S

【分子量】191.25116

【元素组成】C 43.96% H 6.85% N 7.32% O 25.1% S 16.77%

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：(VI)

Condensation of glucosamine (I) with anisaldehyde (II) gave imine (III). Subsequent acetylation of (III) with Ac2O in pyridine produced the tetra O-acetate (IV). The imine group of (IV) was then hydrolyzed with HCl in aqueous acetone to afford, after basic work-up, glucosamine tetraacetate (V), which was coupled with N-acetyl penicillamine using 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate to yield amide (VII). Finally, nitrosation of the mercapto group of (VII) with NaNO2 and HCl furnished the title compound.

参考文献中间体

合成目标

【1】 Butler, A.R.; Megson, I.L.; Greig, I.R. (University of St. Andrews); Nitric oxide donor drugs. WO 9820015 .

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)	24036	(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol; Glucosamine	3416-24-8	C₆H₁₃NO₅	详情	详情
(II)	27251	4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde	123-11-5	C₈H₈O₂	详情	详情
(III)	27252	(3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-2,4,5-triol		C₁₄H₁₉NO₆	详情	详情
(IV)	27253	(2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-3-yl acetate		C₂₂H₂₇NO₁₀	详情	详情
(V)	27254	(2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-aminotetrahydro-2H-pyran-3-yl acetate		C₁₄H₂₁NO₉	详情	详情
(VI)	27255	(2S)-2-(acetamido)-3-methyl-3-sulfanylbutyric acid	59-53-0	C₇H₁₃NO₃S	详情	详情
(VII)	27256	(2R,3R,4R,5R,6S)-5-[[(2S)-2-(acetamido)-3-methyl-3-sulfanylbutanoyl]amino]-4,6-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate		C₂₁H₃₂N₂O₁₁S	详情	详情

Extended Information