کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346948 980286 2009 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and NMR spectroscopic analysis of 3-nitro-pyranoside, 3-nitro-septanoside and 4-nitro-septanoside derivatives by condensation of the anion of nitromethane with glycoside dialdehydes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Synthesis and NMR spectroscopic analysis of 3-nitro-pyranoside, 3-nitro-septanoside and 4-nitro-septanoside derivatives by condensation of the anion of nitromethane with glycoside dialdehydes
چکیده انگلیسی

The utility of the nitroaldol reaction for accessing 3-nitro-pyranoside, 3-nitro-septanoside or 4-nitro-septanoside derivatives, by reaction of the anion of nitromethane with glycoside dialdehydes is demonstrated. Initially, the feasibility of using unprotected glucoside dialdehydes was probed for the synthesis of the septanoside products, but this afforded pyranoside rather than septanoside targets. Subsequent studies utilised protected glycoside dialdehydes within the methodology, which allowed entry into a range of 3-nitro or 4-nitro-septanosides in good yield. NMR spectroscopic analysis allowed determination of the stereochemistry of each of the products thus afforded.

The utility of the nitroaldol reaction for accessing 3-nitro-pyranoside, 3-nitro-septansoide or 4-nitro-septanoside derivatives, by reaction of the anion of nitromethane with glycoside dialdehydes, is described.Figure optionsDownload as PowerPoint slide

Benzyl 3-deoxy-3-nitro-β-d-glucopyranosideC13H17NO7Ee = 100%[α]D20=-29.1 (c 1.01, MeOH)Source of chirality: methyl α-d-glucopyranoside

Methyl 5,7-O-benzylidene-3-deoxy-3-nitro-α-d-glycero-d-altro-septanosideC15H19NO8Ee = 100%[α]D20=+23.7 (c 1.75, MeOH)Source of chirality: methyl α-d-glucopyranoside

Methyl 2-O-benzyl-4-deoxy-4-nitro-7-benzyloxymethyl-α-d-glycero-l-manno-septanosideC22H27NO8Ee = 100%[α]D20=+96.9 (c 1.0, CHCl3)Source of chirality: methyl α-d-glucopyranoside

Methyl 2-O-benzyl-4-deoxy-4-nitro-7-benzyloxymethyl-α-d-glycero-d-talo-septanosideC22H27NO8Ee = 100%[α]D20=+49.4 (c 1.06, CHCl3)Source of chirality: methyl α-d-mannopyranoside

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 18, 23 September 2009, Pages 2162–2166
نویسندگان
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