반응식
C12C[CH:4](C=C1)[C:3](=[O:8])N2.Cl.[NH2:10][C@@H:11]1[CH2:15][C@H:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12]1.[CH3:19]O>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:3]([NH:10][C@@H:11]1[CH2:15][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12]1)(=[O:8])[CH3:4]참가 물질
실험 절차
The recent description of an unequivocal route to 2-azabicyclo[2.2.1]hept-5-en-3-one (1, referring to the corresponding number on the flow sheet) (Jagt et al, J. Org. Chem., 39, 564 (1974)) offers a unique starting point for the synthesis of carbocyclic aminonucleosides of known geometric configuration. Acidic hydrolysis of this compound to cis-4-aminocyclopent-2-ene carboxylic acid hydrochloride, followed by esterification of the carboxyl function in refluxing methanol and subsequent acetylation of the amino group in acetic anhydride-pyridine, gives methyl (+)-cis-4-acetamidocyclopent-2-ene carboxylate (2). Reduction of the methyl ester of 2 gives, after acetylation, acetate 3. Epoxidation of acetate 3 is stereoselective due to the syn-directing allylic amide group, giving only the cis-epoxide 4. Hydrolysis of the easily synthesized epoxide 4 and subsequent acetylation gives a mixture of 5, 6 and 6a.
출처 및 근거
- ORD 기록
- ord-fdcbe764038c4a51b0184f5b06120764
- 출처 데이터셋
- uspto-grants-1979_02
- 특허 번호
- US04138562
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