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Volumn 2, Issue 4, 2005, Pages 316-318

Stereoselective preparation 1-deoxy-homonojirimycin from a β-ketoester bearing sugar

Author keywords

hydroxyester; ketoester; 1 deoxy homnojirimycin; Polyhydroxylated piperidine; Xylofuranose

Indexed keywords

EID: 27644594401 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/1570178054038876 Document Type: Review

Times cited : (9)

References (22)

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21
- 46149106723
- Methyl-(3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O- isopropylidene -α-L-ido-hepto-1,4-furan)-uronate(4, The catalyst was first prepared under argon according to the next procedure: To bis-(2-methylallyl, cycloocta-1,5-diene-ruthenium(II) complex (0.02 equiv, 1.6 mg) and (R)-2,2′-bis(diphenylphosphino)-1,1′- binaphtyl (0.02 equiv, 3.4 mg) in degazed acetone (0.3 ml) was added a methanolic solution of hydrogen bromide (0.15-0.18M, 0.04 equiv, After one hour of stirring, the solvant was evaporated. The β-keto ester 5 (100 mg, 0.3 mmol) in freshly distilled degazed MeOH (0.6 ml, was then cannulated to the catalyst. The reaction mixture was stirred 24 h at 40°C under hydrogen atmosphere. Evaporation of the solvant followed by a purification by flash chromatography (Et2O/pentane: 1/3) allowed pure 4 (100 mg, 99, e.d.>99, α]D 25=-18 (c 1.6, DCM, 1H NMR 2
- 7Si: C 54.23, H 8.57; found: C 54.14, H 8.67.

22
- 46149090724
- 1,5,6-Trideoxy-1,5-imino- D-gluco-heptitol (2, TBAF 1M in THF (1.1 ml) was added to a solution of 9 (329 mg, 0.53 mmol) in THF (2.3 ml, After 1 h of stirring, saturated NH4Cl was added and the mixture was extracted with Et2O. A purification by flash chromatography (AcOEt) led to the expected diol 3 (121 mg, 88, The azide 3 (121 mg, 0.46 mmol) in a solution of TFA in water (3/2, 5 ml) was stirred 2 h at 40°C. PtO2 (10.6 mg, 0.046 mmol) was then added and the reaction mixture was hydrogenolysed at room temperature one night. The catalyst was filtered over celite and washed with MeOH. After concentration, the crude product was dissolved in water, washed with DCM then concentrated to 200 mg of a dark oil. Purification over Amberlyst A-26 (OH, eluted with an aqueous solution of NH4OH 2.5, gave the expected piperidine 2 70 mg, 85% from 3, The optical rotation was measured on
- 25= +30 (c 0.55, MeOH).

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