tert-butyl (1R)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-methylethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】31759

【品名】tert-butyl (1R)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-methylethylcarbamate

【CA登记号】

【分子式】C₁₅H₂₀N₂O₂S₂

【分子量】324.46808

【元素组成】C 55.53% H 6.21% N 8.63% O 9.86% S 19.77%

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：(IV)

Protection of D-alaninol (I) with di-tert-butyl dicarbonate gave rise to carbamate (II). Subsequent Mitsunobu coupling of (II) with 2-mercaptobenzothiazole (III) furnished thioether (IV), which was deprotected with HCl in EtOAc. The resulting amine (V) was condensed with dichloropurine (VI) to afford the chloroadenosine derivative (VII). Finally, cleavage of the acetate esters of (VII) was achieved by treatment with NaOMe in MeOH.

参考文献中间体

合成目标

【1】 Lau, J.; Judge, M.E.; Sheardown, M.J.; Petersen, H.; Shalmi, M.; Knutsen, L.J.S.; Hansen, A.J.; Thomsen, C.; Weis, J.U.; N-substituted adenosines as novel neuroprotective A1 agonists with diminished hypotensive effects. J Med Chem 1999, 42, 18, 3463.

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)	21414	(2R)-2-Amino-1-propanol; D-Alaninol; D-(-)-Alaninol	35320-23-1	C₃H₉NO	详情	详情
(II)	31758	tert-butyl (1R)-2-hydroxy-1-methylethylcarbamate		C₈H₁₇NO₃	详情	详情
(III)	24677	1,3-benzothiazol-2-ylhydrosulfide	149-30-4	C₇H₅NS₂	详情	详情
(IV)	31759	tert-butyl (1R)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-methylethylcarbamate		C₁₅H₂₀N₂O₂S₂	详情	详情
(V)	31760	(2R)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-propanamine; (1R)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-methylethylamine		C₁₀H₁₂N₂S₂	详情	详情
(VI)	25228	(2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate		C₁₆H₁₆Cl₂N₄O₇	详情	详情
(VII)	31761	(2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(6-[[(1R)-2-(1,3-benzothiazol-2-ylsulfanyl)-1-methylethyl]amino]-2-chloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate		C₂₆H₂₇ClN₆O₇S₂	详情	详情

Extended Information