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【结 构 式】

【分子编号】45375

【品名】benzyl [(1S,2R,3S,5R)-3-[(4-methoxybenzyl)oxy]-6-oxabicyclo[3.1.0]hex-2-yl]methyl ether; (1S,2R,3S,5R)-2-[(benzyloxy)methyl]-3-[(4-methoxybenzyl)oxy]-6-oxabicyclo[3.1.0]hexane

【CA登记号】

【 分 子 式 】C21H24O4

【 分 子 量 】340.41916

【元素组成】C 74.09% H 7.11% O 18.8%

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:(II)

The protection of the chiral epoxy-alcohol (I) with Pmb-Cl, NaH and tetrabutylammonium iodide (TBAI) gives the protected compound (II), which is condensed with 2-amino-6-(2-methoxyethoxy)purine (III) in hot DMF to yield the adduct (IV). Elimination of the OH group of (IV) by means of a treatment with phenyl chlorothioformate, followed by a thermal elimination reaction with Bu3SnH and AIBN, affords the carbocyclic purine (V). The selective deprotection of (V) with DDQ in dichloromethane provides the cyclopentanol derivative (VI), which is treated with MsCl and DMAP to give the mesylate (VII).The reaction of (VII) with sodium 2-methoxyethanolate (A) in DMF yields the cyclopentene derivative (VIII), which is treated with AlI3 in hot acetonitrile to afford the carbocyclic guanine derivative (IX). The deprotection of (X) with BF3/Et2O and Ac2O provides the diacetyl derivative (X), which is finally deacetylated to the target chiral compound by means of NH3 in methanol.

1 Jones, M.F.; et al.; Total synthesis of (-)-carbovir. J Chem Soc - Perkins Trans I 1991, 10, 2479.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 45380 sodium 2-methoxy-1-ethanolate 3139-99-9 C3H7NaO2 详情 详情
(I) 29889 (1S,2R,3S,5R)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexan-3-ol C13H16O3 详情 详情
(II) 45375 benzyl [(1S,2R,3S,5R)-3-[(4-methoxybenzyl)oxy]-6-oxabicyclo[3.1.0]hex-2-yl]methyl ether; (1S,2R,3S,5R)-2-[(benzyloxy)methyl]-3-[(4-methoxybenzyl)oxy]-6-oxabicyclo[3.1.0]hexane C21H24O4 详情 详情
(III) 14440 2,5-pyridinedicarboxylic acid 100-26-5 C7H5NO4 详情 详情
(IV) 45376 (1S,2S,3S,5S)-5-[2-amino-6-(2-methoxyethoxy)-9H-purin-9-yl]-2-[(benzyloxy)methyl]-3-[(4-methoxybenzyl)oxy]cyclopentanol C29H35N5O6 详情 详情
(V) 45377 9-[(1R,3R,4S)-3-[(benzyloxy)methyl]-4-[(4-methoxybenzyl)oxy]cyclopentyl]-6-(2-methoxyethoxy)-9H-purin-2-ylamine; 9-[(1R,3R,4S)-3-[(benzyloxy)methyl]-4-[(4-methoxybenzyl)oxy]cyclopentyl]-6-(2-methoxyethoxy)-9H-purin-2-amine C29H35N5O5 详情 详情
(VI) 45378 (1S,2R,4R)-4-[2-amino-6-(2-methoxyethoxy)-9H-purin-9-yl]-2-[(benzyloxy)methyl]cyclopentanol C21H27N5O4 详情 详情
(VII) 45379 9-((1R,3R,4S)-3-[(benzyloxy)methyl]-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentyl)-6-(2-methoxyethoxy)-9H-purin-2-ylamine; 9-((1R,3R,4S)-3-[(benzyloxy)methyl]-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentyl)-6-(2-methoxyethoxy)-9H-purin-2-amine C24H33N5O4S 详情 详情
(VIII) 45381 9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-6-(2-methoxyethoxy)-9H-purin-2-ylamine; 9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-6-(2-methoxyethoxy)-9H-purin-2-amine C21H25N5O3 详情 详情
(IX) 45382 2-amino-9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-1,9-dihydro-6H-purin-6-one C18H19N5O2 详情 详情
(X) 45383 [(1S,4R)-4-[2-(acetamido)-6-oxo-1,6-dihydro-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl acetate C15H17N5O4 详情 详情
Extended Information