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【结 构 式】 
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【分子编号】24621 【品名】1-[(chlorocarbonyl)sulfanyl]cyclopentane 【CA登记号】 |
【 分 子 式 】C6H9ClOS 【 分 子 量 】164.65556 【元素组成】C 43.77% H 5.51% Cl 21.53% O 9.72% S 19.47% |
合成路线1
该中间体在本合成路线中的序号：(XIX)Acid (XV) was coupled with protected amino acid (XVI) to give amide (XVII), and the Boc protecting group of (XVII) was then removed under acidic conditions. The resulting amine (XVIII) was condensed with cyclopentyl chlorothioformate (XIX) to provide thiocarbamate (XX). Finally, the title compound was obtained by trifluoroacetic acid-promoted cleavage of the trityl protecting group of (XIX).
| 【1】 Worland, S.T.; Ferre, R.A.; Patick, A.K.; Prins, T.J.; Meador, J.W. III; Zhou, R.; Dragovich, P.S.; Fuhrman, S.A.; Matthews, D.A.; Ford, C.E.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J Med Chem 1999, 42, 7, 1203. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 24639 | (2R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-6-methyl-4-oxoheptanoic acid | C20H29NO5 | 详情 | 详情 | |
| (XVI) | 24618 | ethyl (E,4S)-4-amino-7-oxo-7-(tritylamino)-2-heptenoate | C28H30N2O3 | 详情 | 详情 | |
| (XVII) | 24640 | ethyl (E,4S)-4-([(2R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-6-methyl-4-oxoheptanoyl]amino)-7-oxo-7-(tritylamino)-2-heptenoate | C48H57N3O7 | 详情 | 详情 | |
| (XVIII) | 24641 | ethyl (E,4S)-4-[[(2R,5S)-5-amino-2-benzyl-6-methyl-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C43H49N3O5 | 详情 | 详情 | |
| (XIX) | 24621 | 1-[(chlorocarbonyl)sulfanyl]cyclopentane | C6H9ClOS | 详情 | 详情 | |
| (XX) | 24642 | ethyl (E,4S)-4-[((2R,5S)-2-benzyl-5-[[(cyclopentylsulfanyl)carbonyl]amino]-6-methyl-4-oxoheptanoyl)amino]-7-oxo-7-(tritylamino)-2-heptenoate | C49H57N3O6S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIX)Acid (XV) was coupled with protected amino acid (XVI) to give amide (XVII), and the Boc protecting group of (XVII) was then removed under acidic conditions. The resulting amine (XVIII) was condensed with cyclopentyl chlorothioformate (XIX) to provide thiocarbamate (XX). Finally, the title compound was obtained by trifluoroacetic acid-promoted cleavage of the trityl protecting group of (XIX).
| 【1】 Worland, S.T.; Ferre, R.A.; Patick, A.K.; Prins, T.J.; Meador, J.W. III; Zhou, R.; Dragovich, P.S.; Fuhrman, S.A.; Matthews, D.A.; Ford, C.E.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J Med Chem 1999, 42, 7, 1203. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 24626 | (3R,5S)-5-[(1S)-1-azido-2-methylpropyl]-3-(4-methylbenzyl)dihydro-2(3H)-furanone | C16H21N3O2 | 详情 | 详情 | |
| (XVI) | 24618 | ethyl (E,4S)-4-amino-7-oxo-7-(tritylamino)-2-heptenoate | C28H30N2O3 | 详情 | 详情 | |
| (XVII) | 24630 | ethyl (E,4S)-4-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-6-methyl-2-(4-methylbenzyl)-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C49H59N3O7 | 详情 | 详情 | |
| (XVIII) | 24631 | ethyl (E,4S)-4-[[(2R,5S)-5-amino-6-methyl-2-(4-methylbenzyl)-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C44H51N3O5 | 详情 | 详情 | |
| (XIX) | 24621 | 1-[(chlorocarbonyl)sulfanyl]cyclopentane | C6H9ClOS | 详情 | 详情 | |
| (XX) | 24632 | ethyl (E,4S)-4-[[(2R,5S)-5-[[(cyclopentylsulfanyl)carbonyl]amino]-6-methyl-2-(4-methylbenzyl)-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C50H59N3O6S | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(XIX)Acid (XV) was coupled with protected amino acid (XVI) to give amide (XVII), and the Boc protecting group of (XVII) was then removed under acidic conditions. The resulting amine (XVIII) was condensed with cyclopentyl chlorothioformate (XIX) to provide thiocarbamate (XX). Finally, the title compound was obtained by trifluoroacetic acid-promoted cleavage of the trityl protecting group.
| 【1】 Worland, S.T.; Ferre, R.A.; Patick, A.K.; Prins, T.J.; Meador, J.W. III; Zhou, R.; Dragovich, P.S.; Fuhrman, S.A.; Matthews, D.A.; Ford, C.E.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J Med Chem 1999, 42, 7, 1203. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 24617 | (2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoic acid | C20H28FNO5 | 详情 | 详情 | |
| (XVI) | 24618 | ethyl (E,4S)-4-amino-7-oxo-7-(tritylamino)-2-heptenoate | C28H30N2O3 | 详情 | 详情 | |
| (XVII) | 24619 | ethyl (E,4S)-4-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C48H56FN3O7 | 详情 | 详情 | |
| (XVIII) | 24620 | ethyl (E,4S)-4-[[(2R,5S)-5-amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C43H48FN3O5 | 详情 | 详情 | |
| (XIX) | 24621 | 1-[(chlorocarbonyl)sulfanyl]cyclopentane | C6H9ClOS | 详情 | 详情 | |
| (XX) | 24622 | ethyl (E,4S)-4-[[(2R,5S)-5-[[(cyclopentylsulfanyl)carbonyl]amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-7-oxo-7-(tritylamino)-2-heptenoate | C49H56FN3O6S | 详情 | 详情 |