کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350703 980457 2006 11 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-l-lyxofuranose
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-l-lyxofuranose
چکیده انگلیسی

Two anomeric spirodiketopiperazines and one spirohydantoin of 6-deoxy-l-lyxofuranose have been prepared from l-fucono-δ-lactone via ring contraction to the corresponding tetrahydrofuran carboxylate and anomeric functionalization including regioselective bromination and azide displacement.

The anomeric spirodiketopiperazines and spirohydantoin of 6-deoxy-l-lyxofuranose have been prepared from l-fucose.Figure optionsDownload as PowerPoint slide

2-Trifluoromethanesulfonyl-3,4-O-isopropylidene-l-fucono-1,5-lactoneC10H13F3O7S[α]D22=-64.3 (c 1.11, CHCl3)Source of chirality: l-fucose

Methyl 2,5-anhydro-6-deoxy-3,4-O-isopropylidene-l-talonateC12H22O5[α]D22=-33.8 (c 1.95, CHCl3)Source of chirality: l-fucose

Methyl 2,5-anhydro-2-bromo-6-deoxy-3,4-O-isopropylidene-l-galactonateC10H15BrO5[α]D22=-199 (c 1.60, CHCl3)Source of chirality: l-fucose

Methyl 2,5-anhydro-2-azido-6-deoxy-3,4-O-isopropylidene-l-talonateC10H15N3O5[α]D22=-35.3 (c 1.23, CHCl3)Source of chirality: l-fucose

3,4-O-Isopropylidene-l-talono-1,5-lactoneC9H14O5[α]D22=-105.4 (c 0.74, CHCl3)Source of chirality: l-fucose

2-Trifluoromethanesulfonyl-3,4-O-isopropylidene-l-talono-1,5-lactoneC10H13F3O7S[α]D22=-56.9 (c 0.91, CHCl3)Source of chirality: l-fucose

Methyl 2,5-anhydro-6-deoxy-3,4-O-isopropylidene-l-galactonateC10H16O5[α]D22=-53.9 (c 1.21, CHCl3)Source of chirality: l-fucose

Methyl 2-amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-l-galactonateC10H17NO5[α]D23=-27.7 (c 0.95, CHCl3)Source of chirality: l-fucose

Methyl N-2-(benzyloxycarbonylglycylamino)-2,5-anhydro-3,4-O-isopropylidene-6-deoxy-l-talonateC20H26N2O8[α]D22=-3.2 (c 1.19, CHCl3)Source of chirality: l-fucose

Methyl N-2-(benzyloxycarbonylglycylamino)-2,5-anhydro-3,4-O-isopropylidene-6-deoxy-l-galactonateC20H26N2O8[α]D22=-49 (c 0.42, CHCl3)Source of chirality: l-fucose

(2S,3R,4R,5R)-3,4-O-Isopropylidene-2-methyl-6,9-diaza-1-oxaspiro-[4.5]-decane-7,10-dioneC11H16N2O5[α]D22=-56.1 (c 0.51, CHCl3)Source of chirality: l-fucose

(2S,3R,4R,5S)-3,4-O-Isopropylidene-2-methyl-6,9-diaza-1-oxaspiro-[4.5]-decane-7,10-dioneC11H16N2O5[α]D22=-152.1 (c 0.61, CH3OH)Source of chirality: l-fucose

(2S,3R,4R,5R)-3,4-O-Isopropylidene-2-methyl-6,8-diaza-1-oxaspiro-[4.4]-nonane-7,9-dioneC10H14N2O5[α]D22=-72.6 (c 0.58, CHCl3)Source of chirality: l-fucose

(2S,3R,4R,5R)-2-Methyl-6,9-diaza-1-oxaspiro-[4.5]-decane-7,10-dioneC10H18N2O5[α]D22=-1.1 (c 0.43, CH3OH)Source of chirality: l-fucose

(2S,3R,4R,5S)-2-Methyl-6,9-diaza-1-oxaspiro-[4.5]-decane-7,10-dioneC10H18N2O5[α]D22=-0.3 (c 0.41, CH3OH)Source of chirality: l-fucose

(2S,3R,4R,5R)-2-Methyl-6,8-diaza-1-oxaspiro-[4.4]-nonane-7,9-dioneC7H10N2O5[α]D22=-23.2 (c 0.57, CH3OH)Source of chirality: l-fucose

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 15, 11 September 2006, Pages 2276–2286
نویسندگان
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