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【结 构 式】 
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【分子编号】21978 【品名】(2S,3R,4S)-3-(acetamido)-4-(acetoxy)-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylic acid 【CA登记号】 |
【 分 子 式 】C15H23NO7 【 分 子 量 】329.35016 【元素组成】C 54.7% H 7.04% N 4.25% O 34.01% |
合成路线1
该中间体在本合成路线中的序号：(XII)Aldehyde (XI) was further converted to unsaturated acid (XII) with sodium chlorite and sulfamic acid. Acid (XII) was converted to methyl ester (XIII) by treatment with N,N,N',N'-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (TBTU) and MeOH, and then cyclized to oxazoline (XIV) using trimethylsilyl triflate. Opening of the oxazoline (XIV) with trimethylsilyl azide in tert-butanol gave azide (XV), together with its epimer. Reduction of azide (XV) with SnCl2 gave amine (XVI). Finally, hydrolysis of the methyl ester of (XVI) with aqueous triethylamine afforded the target carboxylic acid.
| 【1】 Smith, P.W.; Robinson, J.E.; Evans, D.N.; Sollis, S.L.; Trivedi, N.; Bethell, R.C.; Howes, P.D.; Sialidase inhibitors related to zanamivir: Synthesis and biological evaluation of 4H-pyran 6-ether and ketone. Bioorg Med Chem Lett 1999, 9, 4, 601. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 21977 | (2R,3R,4R,5R,6S)-3-(acetamido)-5-(acetoxy)-2-(1-ethylpropoxy)-6-formyltetrahydro-2H-pyran-4-yl acetate | C17H27NO8 | 详情 | 详情 | |
| (XII) | 21978 | (2S,3R,4S)-3-(acetamido)-4-(acetoxy)-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylic acid | C15H23NO7 | 详情 | 详情 | |
| (XIII) | 21979 | methyl (2R,3R,4S)-3-(acetamido)-4-(acetoxy)-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylate | C16H25NO7 | 详情 | 详情 | |
| (XIV) | 21980 | methyl (3aR,4R,7aR)-4-(1-ethylpropoxy)-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate | C14H21NO5 | 详情 | 详情 | |
| (XV) | 21981 | methyl (2R,3R,4S)-3-(acetamido)-4-azido-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylate | C14H22N4O5 | 详情 | 详情 | |
| (XVI) | 21982 | methyl (2R,3R,4S)-3-(acetamido)-4-amino-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylate | C14H24N2O5 | 详情 | 详情 |