2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】59532

【品名】2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate

【CA登记号】

【分子式】C₂₁H₂₆N₆O₆

【分子量】458.47428

【元素组成】C 55.02% H 5.72% N 18.33% O 20.94%

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：(III)

Acyclovir (I) was coupled with N-Cbz-L-valine (II) in the presence of DCC and DMAP to afford the Cbz-protected valyl ester (III). The N-benzyloxycarbonyl group of (III) was then removed by either hydrogenation over Pd/C or by transfer hydrogenation in the presence of formic acid.

参考文献中间体

合成目标

【1】 Tak, R.V.; et al.; Transport of acyclovir ester prodrugs through rabbit cornea and SIRC-rabbit corneal epithelial cell line. J Pharm Sci 2001, 90, 10, 1505.
【2】 Krenitsky, T.A.; Beauchamp, L.M. (GlaxoSmithKline plc); Therapeutic nucleosides. AU 8820978; EP 0308065; EP 0596542; JP 1989068373; JP 1991115284; US 4957924; US 5061708 .
【3】 Partin, J.M.; Winnike, R.A.; Carter, B.H.; Lake, P.G.; Varlashkin, P.G.; Grubb, W.B. III; Conway, G.A.; Skinner, D.M.; Whatrup, D.J. (GlaxoSmithKline plc); Guanine deriv.. WO 9622291 .
【4】 Beauchamp, L.M.; et al.; Amino acid ester prodrugs of acyclovir. Antivir Chem Chemother 1992, 3, 3, 157.

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)	28279	2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one	59277-89-3	C₈H₁₁N₅O₃	详情	详情
(II)	18092	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid		C₁₃H₁₇NO₄	详情	详情
(III)	59532	2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoate		C₂₁H₂₆N₆O₆	详情	详情

Extended Information