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【结 构 式】

【分子编号】10037

【品名】(2S,5S)-2-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-5-[benzyl[(2-phenylacetyl)oxy]amino]hexanoic acid

【CA登记号】

【 分 子 式 】C30H35N7O7

【 分 子 量 】605.65088

【元素组成】C 59.49% H 5.82% N 16.19% O 18.49%

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:(XXI)

The aldehyde (XIII) is submitted to a Wittig condensation with N-acetyl-2-(diphenylphosphoryl)glycine (XIV) and potassium tert-butoxide in dichloromethane giving a mixture of the (Z)- and (E)-isomers (XV) and (XVI), respectively. The regiocontrolled hydrogenation of this mixture with H2 over a chiral rhodium catalyst in methanol yields the saturated (S,S)-isomer (XVII), which is submitted to a selective deprotection of its sugar moiety, followed by acetylation of the resulting free hydroxy groups with acetic anhydride in dioxane to afford the triacetoxy compound (XVIII). The condensation of (XVIII) with N6-benzoyladenine (XIX) by means of trimethylsilyl trifluoromethanesulfonate gives the adenosine derivative (XX), which is treated with K2CO3 and hydrazine to eliminate the acetyl and benzoyl groups yielding (XXI). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in methanol.

1 Ghosh, A.K.; Liu, W.M.; Total synthesis of (+)-sinefungin. J Org Chem 1996, 61, 18, 6175.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 10028 Benzyl (1R)-1-[[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl]-3-oxopropyl(benzyl)carbamate C27H33NO7 详情 详情
(XIV) 10030 Ethyl 2-(acetamido)-2-(diphenoxyphosphino)acetate C18H20NO5P 详情 详情
(XV) 10031 Ethyl (E,5S)-6-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(acetamido)-5-[benzyl[(benzyloxy)carbonyl]amino]-2-hexenoate C33H42N2O9 详情 详情
(XVI) 10032 Ethyl (Z,5S)-6-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(acetamido)-5-[benzyl[(benzyloxy)carbonyl]amino]-2-hexenoate C33H42N2O9 详情 详情
(XVII) 10033 Ethyl (2S,5S)-6-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(acetamido)-5-[benzyl[(benzyloxy)carbonyl]amino]hexanoate C33H44N2O9 详情 详情
(XVIII) 10034 Ethyl (2S,5S)-2-(acetamido)-5-[benzyl[(2-phenylacetyl)oxy]amino]-6-[(2R,3R,4R)-3,4,5-tris(acetoxy)tetrahydro-2-furanyl]hexanoate C35H44N2O12 详情 详情
(XIX) 10035 N-(9H-Purin-6-yl)benzamide; N6-Benzoyladenine 4005-49-6 C12H9N5O 详情 详情
(XX) 10036 ethyl (2S,5S)-2-(acetamido)-5-[benzyl[(2-phenylacetyl)oxy]amino]-6-[(2R,3R,4R,5R)-3,4-bis(acetoxy)-5-[6-(benzoylamino)-9H-purin-9-yl]tetrahydro-2-furanyl]hexanoate C45H49N7O11 详情 详情
(XXI) 10037 (2S,5S)-2-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-5-[benzyl[(2-phenylacetyl)oxy]amino]hexanoic acid C30H35N7O7 详情 详情
Extended Information