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【结 构 式】

【分子编号】29245

【品名】(fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane

【CA登记号】20808-12-2

【 分 子 式 】C7H7FO2S

【 分 子 量 】174.1957832

【元素组成】C 48.27% H 4.05% F 10.91% O 18.37% S 18.41%

与该中间体有关的原料药合成路线共 5 条

合成路线1

该中间体在本合成路线中的序号:(B)

The protection of cytidine (I) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (II) and dimethylformamide dimethylacetal (A) in pyridine gives the fully protected cytidine (III), which is oxidized with oxalyl chloride in DMSO/dichloromethane yielding the 2'-deoxy-2'-oxo derivative (IV). The reaction of (IV) with fluoromethyl phenyl sulfone (B) by means of diethyl chlorophosphate and lithium hexamethyldisylazide in THF affords the fluorovinyl sulfone (V) as a mixture of (E) and (Z) isomers that is separated by flash chromatography. The (Z)-isomer (V) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VI), which is finally treated with KF in refluxing methanol to afford the target compound.

1 Donaldson, R.E. (Aventis Pharmaceuticals, Inc.); Monohydrate of (E)-2'-deoxy-2'-(fluoromethylene)cytidine. WO 9518815 .
2 Mathews, D.P.; McCarthy, J.R.; Sabol, J.S. (Aventis Pharmaceuticals, Inc.); A process for the preparation of ribonucleotide reductase inhibitors. WO 9323414 .
3 Snyder, R.D. (Aventis Pharmaceuticals, Inc.); Method of treating a neoplastic disease state by conjunctive therapy with 2'-fluoromethylidene derivs. and radioation or chemotherapy. WO 9601638 .
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) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(B) 29245 (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane 20808-12-2 C7H7FO2S 详情 详情
(I) 27920 Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone 65-46-3 C9H13N3O5 详情 详情
(II) 29242 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane 69304-37-6 C12H28Cl2OSi2 详情 详情
(III) 29243 N'-[1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H44N4O6Si2 详情 详情
(IV) 29244 N'-[1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H42N4O6Si2 详情 详情
(V) 29246 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(VI) 29247 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
(C) 23623 Chlorophosphoric acid ethyl ester;Phosphorochloridic acid diethyl ester;Diethyl chlorophosphate;diethyl phosphorochloridate 814-49-3 C4H10ClO3P 详情 详情

合成路线2

该中间体在本合成路线中的序号:(A)

The acetylation of uridine (I) with acetic anhydride gives the 2',3',5'-triacetyl derivative (II), which is treated with SOCl2 and sodium ethoxide yielding the 4-ethoxypyrimidinone (III). The partial protection of (III) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (IV) yields the silylated compound (V), which is oxidized with oxalyl chloride to the silylated furanone (VI). The reaction of (VI) with fluoromethyl phenyl sulfone (A) by means of diethyl chlorophosphate (B) and lithium hexamethyldisylazide in THF affords the fluorovinyl sulfone (VII) as a mixture of (E) and (Z) isomers that is separated by flash chromatography. The (Z)-isomer (VII) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VIII), which is finally treated with CsF and NH3 in refluxing methanol to afford the target compound.

1 Sunkara, P.S.; McCarthy, J.R.; Matthews, D.P.; et al.; Design of a fluoro-olefin cytidine nucleoside as a bioprecursor of a mechanism-based inhibitor of ribonucleotide reductase. ACS Symp Ser 1996, 639, 246.
2 McCarthy, J.R.; et al.; Stereospecific synthesis of 1-fluoro olefins via (fluorovinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry. Tetrahedron 1996, 52, 1, 45.
3 Matthews, D.P.; et al.; Improved synthesis of (E)-2'-deoxy-2'-(fluoromethylene)cytidine - A potent inhibitor of ribonucleotide diphosphate reductase. Nucleosides Nucleotides 1993, 12, 2, 115.
4 McCarthy, J.R.; Edwards, M.L.; Matthews, D.P. (Merrell Pharmaceuticals, Inc.); Novel 2'-halomethylidene, 2'-ethenylidene and 2'-ethynyl cytidine, uridine and guanosine derivs.. EP 0372268; JP 1990178272; US 5378693 .
5 McCarthy, J.R.; Matthews, D.P.; Bitonti, A.J.; Edwards, M.L. (Merrell Pharmaceuticals, Inc.); Treatment of carcinoma by administration of 2'-halomethylidenyl-2'-deoxynucleosides. US 5607925 .
6 McCarthy, J.R.; Matthews, D.P.; Edwards, M.L. (Merrell Pharmaceuticals, Inc.); 2'-Ethenylidene cytidine, uridine and guanosine derivs.. US 5616702 .
7 McCarthy, J.R.; et al.; Stereospecific method to E and Z terminal fluoro olefins and its application to the synthesis of 2'-deoxy-2'-fluoromethylene nucleosides as potential inhibitors of ribonucleoside diphosphate reductase. J Am Chem Soc 1991, 113, 19, 7439.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 23623 Chlorophosphoric acid ethyl ester;Phosphorochloridic acid diethyl ester;Diethyl chlorophosphate;diethyl phosphorochloridate 814-49-3 C4H10ClO3P 详情 详情
(A) 29245 (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane 20808-12-2 C7H7FO2S 详情 详情
(I) 11996 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine 58-96-8 C9H12N2O6 详情 详情
(II) 29248 (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl acetate C15H18N2O9 详情 详情
(III) 29249 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-4-ethoxy-2(1H)-pyrimidinone C11H16N2O6 详情 详情
(IV) 29242 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane 69304-37-6 C12H28Cl2OSi2 详情 详情
(V) 29250 1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-4-ethoxy-2(1H)-pyrimidinone C23H42N2O7Si2 详情 详情
(VI) 29251 1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-4-ethoxy-2(1H)-pyrimidinone C23H40N2O7Si2 详情 详情
(VII) 29252 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-ethoxy-2(1H)-pyrimidinone C30H45FN2O8SSi2 详情 详情
(VIII) 29253 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-ethoxy-2(1H)-pyrimidinone C36H67FN2O6Si2Sn 详情 详情

合成路线3

该中间体在本合成路线中的序号:(B)

The protection of labeled cytidine (I) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (II) and dimethylformamide dimethylacetal (A) in pyridine gives the fully protected cytidine (III), which is oxidized with oxalyl chloride in DMSO/dichloromethane yielding the 2'-deoxy-2'-oxo derivative (IV). The reaction of (IV) with fluoromethyl phenyl sulfone (B) by means of diethyl chlorophosphate and lithium hexamethyldisylazide in THF affords the fluorovinyl sulfone (V) as a mixture of (E) and (Z) isomers that is separated by flash chromatography. The (Z)-isomer (V) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VI), which is finally treated with KF in refluxing methanol to afford the labeled target compound.

1 Wagner, E.R.; et al.; Radiolabeling of ribonucleotide diphosphate reductase inhibitor (E)-2'-deoxy-2'-(fluoromethylene)cytidine. Synthesis and Applications of Isotopically Labelled Compounds 1994, 659 (paper 118).
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) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(B) 29245 (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane 20808-12-2 C7H7FO2S 详情 详情
(I) 27920 Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone 65-46-3 C9H13N3O5 详情 详情
(I) 45211 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone C9H13N3O5 详情 详情
(II) 29242 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane 69304-37-6 C12H28Cl2OSi2 详情 详情
(III) 29243 N'-[1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H44N4O6Si2 详情 详情
(III) 45212 N'-[1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H44N4O6Si2 详情 详情
(IV) 29244 N'-[1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H42N4O6Si2 详情 详情
(IV) 45213 N'-[1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H42N4O6Si2 详情 详情
(V) 29246 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(V) 45214 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(VI) 29247 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
(VI) 45215 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
(C) 23623 Chlorophosphoric acid ethyl ester;Phosphorochloridic acid diethyl ester;Diethyl chlorophosphate;diethyl phosphorochloridate 814-49-3 C4H10ClO3P 详情 详情

合成路线4

该中间体在本合成路线中的序号:(V)

The protection of cytidine (I) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (II) and dimethylformamide dimethylacetal (A) in pyridine gives the fully protected cytidine (III), which is oxidized with oxalyl chloride in DMSO/dichloromethane yielding the 2'-deoxy-2'-oxo derivative (IV). The reaction of (IV) with labeled fluoromethyl phenyl sulfone (V) by means of diethyl chlorophosphate (B) and lithium hexamethyldisylazide in THF affords the fluorovinyl sulfone (VI) as a mixture of (E) and (Z) isomers that is separated by flash chromatography. The (Z)-isomer (VI) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VII), which is finally treated with KF in refluxing methanol to afford the labeled target compound.

1 Wagner, E.R.; et al.; Radiolabeling of ribonucleotide diphosphate reductase inhibitor (E)-2'-deoxy-2'-(fluoromethylene)cytidine. Synthesis and Applications of Isotopically Labelled Compounds 1994, 659 (paper 118).
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) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(B) 23623 Chlorophosphoric acid ethyl ester;Phosphorochloridic acid diethyl ester;Diethyl chlorophosphate;diethyl phosphorochloridate 814-49-3 C4H10ClO3P 详情 详情
(I) 27920 Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone 65-46-3 C9H13N3O5 详情 详情
(II) 29242 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane 69304-37-6 C12H28Cl2OSi2 详情 详情
(III) 29243 N'-[1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H44N4O6Si2 详情 详情
(IV) 29244 N'-[1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydro-4-pyrimidinyl]-N,N-dimethyliminoformamide C24H42N4O6Si2 详情 详情
(V) 29245 (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane 20808-12-2 C7H7FO2S 详情 详情
(V) 45218 fluoromethyl phenyl sulfone; (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane C7H7FO2S 详情 详情
(VI) 29246 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(VI) 45219 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(VII) 29247 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
(VII) 45220 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
(VIII) 29254 methyl(oxo)phenyl-lambda(4)-sulfane 1193-82-4 C7H8OS 详情 详情
(VIII) 45216 methyl phenyl sulfoxide; methyl(oxo)phenyl-lambda(4)-sulfane C7H8OS 详情 详情
(IX) 29255 fluoromethyl phenyl sulfide C7H7FS 详情 详情
(IX) 45217 1-[(fluoromethyl)sulfanyl]benzene; fluoromethyl phenyl sulfide C7H7FS 详情 详情

合成路线5

该中间体在本合成路线中的序号:(V)

A new synthesis of tezacitabine has been described: Protection of cytidine (I) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (II) in pyridine gives the protected cytidine (III), which is oxidized with trifluoroacetic anhydride (TFAA)/DMSO in THF and treated with TEA to yield the 2'-deoxy-2'-oxocytidine derivative (IV). Condensation of (IV) with fluoromethyl phenyl sulfone (V) by means of diethyl chlorophosphate and lithium hexamethyldisilazide in THF affords the fluorovinyl sulfone (VI) as a mixture of (E)- and (Z)-isomers that is separated by flash chromatography. The desired (Z)-isomer (VI) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VII), which is finally treated with KF in refluxing methanol.

1 Duguid, R.J.; Appell, R.B.; New synthesis of protected ketonucleoside by a non-cryogenic oxidation with TFAA/DMSO. Org Process Res Dev 2000, 4, 3, 172.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
23623 Chlorophosphoric acid ethyl ester;Phosphorochloridic acid diethyl ester;Diethyl chlorophosphate;diethyl phosphorochloridate 814-49-3 C4H10ClO3P 详情 详情
(I) 27920 Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone 65-46-3 C9H13N3O5 详情 详情
(II) 29242 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane 69304-37-6 C12H28Cl2OSi2 详情 详情
(III) 46713 1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-4-amino-2(1H)-pyrimidinone C21H39N3O6Si2 详情 详情
(IV) 46714 1-[(6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-4-amino-2(1H)-pyrimidinone C21H37N3O6Si2 详情 详情
(V) 29245 (fluoromethyl)(dioxo)phenyl-lambda(6)-sulfane 20808-12-2 C7H7FO2S 详情 详情
(VI) 29246 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(phenylsulfonyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C28H42FN3O7SSi2 详情 详情
(VII) 29247 1-[(6aR,8R,9aS)-9-[(Z)-fluoro(tributylstannyl)methylidene]-2,2,4,4-tetraisopropyldihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8(8H)-yl]-4-amino-2(1H)-pyrimidinone C34H64FN3O5Si2Sn 详情 详情
Extended Information