کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346198 980247 2013 12 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins
چکیده انگلیسی

The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from d-mannitol, has been carried out. Two different synthetic strategies were followed for each of the vinyl-nitro precursors. Many of the azasugars synthesized showed inhibition in the micromolar range when tested against various glycosidase enzymes, opening up the possibility of modifying structural features for better and selective inhibition.

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(3aR,7S,7aR)-Benzyl 7-allyl-2,2-dimethyltetrahydro-[1,3]dioxolo-[4,5-c]pyridine-5(6H)-carboxylateC19H25NO4[α]D25=-30.0 (c 0.9, CH2Cl2)Source of chirality: d-mannitol, allyl Grignard reactionAbsolute configuration: (3aR,7S,7aR)

(3aR,7S,7aR)-5-Butyl-2,2-dimethyl-7-propylhexahydro-[1,3]dioxo-lo[4,5-c]pyridineC15H29NO2[α]D25=+2.7 (c 0.75, CH2Cl2)Source of chirality: d-mannitol, allyl Grignard reactionAbsolute configuration: (3aR,7S,7aR)

(3R,4R,5R)-1-Butyl-5-propylpiperidine-3,4-diolC12H25NO2[α]D25=+6.7 (c 0.3, EtOH)Source of chirality: d-mannitol, allyl Grignard reactionAbsolute configuration: (3R,4R,5R)

(S)-tert-Butyl 5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)-5,6-dihydro-pyridine-1(2H)-carboxylateC18H29NO4[α]D25=+45.0 (c 0.9, CH2Cl2)Source of chirality: d-mannitol, vinyl Grignard reactionAbsolute configuration: (S,S)

(3S,4R,5S)-5-((S)-1,2-Dihydroxyethyl)piperidine-3,4-diolC7H15NO4[α]D25=-36.8 (c 0.95, MeOH)Source of chirality: d-mannitol, vinyl Grignard reaction, dihydroxylationAbsolute configuration: (3S,4R,5S)(S)

(3S,4R,5S)-tert-Butyl 3,4-dihydroxy-5-((S)-1,4-dioxaspiro[4.5]-decan-2-yl)piperidine-1-carboxylateC18H31NO6[α]D25=+5.7 (c 0.35, CH2Cl2)Source of chirality: d-mannitol, vinyl Grignard reaction, dihydroxylationAbsolute configuration: (3S,4R,5S)(S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 24, Issue 23, 15 December 2013, Pages 1502–1513
نویسندگان
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