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【结 构 式】

【分子编号】21981

【品名】methyl (2R,3R,4S)-3-(acetamido)-4-azido-2-(1-ethylpropoxy)-3,4-dihydro-2H-pyran-6-carboxylate

【CA登记号】

【 分 子 式 】C14H22N4O5

【 分 子 量 】326.35264

【元素组成】C 51.53% H 6.79% N 17.17% O 24.51%

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:(XV)

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
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