Stereoselective catalytic double osmylation of 1,2-dihydropyridines leading to amino-arabinose and to amino-altrose derivatives and to potential glycosidase inhibitors.

Tschamber, Théophile; Backenstrass, Frédérique; Neuburger, M.; Zehnder, Margareta; Strieth, Jacques

doi:10.1016/s0040-4020(01)80825-5

Cited by 24 publications

(8 citation statements)

References 17 publications

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“…7, 26.1, 27.1, 27.4, 51.8, 55.1, 65.5, 72.8, 74.8, 76.3, 78.3, 109.5, 110.0, 119.9, 120.1, 125.7, 126.1, 127.1, 127.3, 127.4, 127.8, 128.4, 128.5, 128.6, 140.3 1, 27.3, 51.8, 55.0, 65.1, 69.0, 72.8, 77.9, 78.2, 110.0, 120.0, 120.2, 125.4, 126.0, 127.0, 127.4, 127.4, 128.4, 128.5, 128.7, 140.4, 141.0, 143.8, 147.8, 148.7, 173.9 1, 27.1, 51.8, 55.4, 61.8, 72.9, 76.9, 78.3, 109.4, 120.0, 120.2, 125.5, 126.1, 126.7, 127.4, 127.8, 128.5, 128.6, 128.7, 140.4, 141.0, 143.8, 147.9, 148.6, 173.9 1, 37.7, 51.9, 55.2, 68.4, 72.9, 74.6, 77.6, 110.3, 120.0, 120.2, 125.3, 126.6, 126.7, 127.4, 127.5, 128.1, 128.5, 128.6, 128.8, 140.3, 141.0, 143.7, 147.8, 148.4, 173.5. Anal. calcd for C 29 H 31 NO 7 S: C,64.79;H,5.81;N,2.61. Found: C,64.92;H,5.97;N,2.67.…”

Section: Methodsmentioning

confidence: 99%

“…9, 27.2, 37.7, 52.9, 62.8, 68.7, 72.4, 75.3, 80.1, 109.8, 120.1, 120.2, 125.1, 125.5, 126.0, 127.4, 128.0, 128.2, 128.4, 128.6, 128.7, 140.2, 140.6, 144.8, 148.7, 150.6. Anal. calcd for C 28 H 31 NO 6 : C,70.42;H,6.54;N,2.93. Found: C,70.71;H,6.77;N,2.98.…”

Section: R3r4r-34-dihydroxyproline (3)mentioning

confidence: 99%

“…1 = 27.0, 27.2, 37.7, 51.9, 55.0, 67.5, 71.3, 72.9, 76.0, 77.6, 110.2, 120.0, 120.3, 125.3, 126.0, 126.9, 127.4, 127.5, 128.1, 128.5, 128.6, 128.9, 140.4, 141.6, 143.7, 147.8, 148.6, 173.7. Anal. calcd for C 30 H 33 NO 7 S: C,65.32;H,6.03;N,2.54. Found: C,65.41;H,6.35;N,2.58.…”

Section: 4-dideoxy-14-imino-l-xylitol (1)mentioning

confidence: 99%

“…calcd for C 10 H 17 NO 5 : C, 51.94; H, 7.41;N,6.06. Found: C,52.11;H,7.59;N,6.25. Dideoxy-1,5-imino-3,4-O-isopropyliden-L-iditol (13) To an ice-cooled suspension of LiAlH 4 (31 mg, 0.82 mmol) in THF (2 mL) was added a solution of 12 (0.16 g, 0.68 mmol) in THF (1 mL).…”

Section: Methyl 15-dideoxy-15-imino-34-o-isopropyliden-l-idonate (12)mentioning

confidence: 99%

See 3 more Smart Citations

A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

Lee¹,

Jeong²,

Yang³

et al. 2000

Synthesis

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Section: Methodsmentioning

confidence: 99%

Section: R3r4r-34-dihydroxyproline (3)mentioning

confidence: 99%

Section: 4-dideoxy-14-imino-l-xylitol (1)mentioning

confidence: 99%

Section: Methyl 15-dideoxy-15-imino-34-o-isopropyliden-l-idonate (12)mentioning

confidence: 99%

See 2 more Smart Citations

A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

Lee¹,

Jeong²,

Yang³

et al. 2000

Synthesis

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“…Backenstrass and Streith [38] evaluated these molecules 61–63 for their antiviral activity in CEM‐T4 cells infected with HIV 1 (strain GB 8). Their activity was assessed by light microscopic measurement of inhibition of syncytium formation.…”

Section: Biological Activities Of 345‐trihydroxypiperidines N‐ and mentioning

confidence: 99%

Biological activities of 3,4,5‐trihydroxypiperidines and their N‐ and O‐derivatives

et al. 2018

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3,4,5-Trihydroxypiperidines belong to the family of 1,5-dideoxy-1,5-iminosugar natural products and are structural analogues of pentose monosaccharides in the pyranose form. The biological activities of these apparently structurally simple molecules and their N- and O-alkylated and -arylated derivatives are no less remarkable than their C-6 hydroxymethyl counterparts of the hexoses (such as 1-deoxynojirimycin, DNJ). Their biological profiles indicate that the hydroxymethyl branch is crucial to neither potency nor selectivity, with O-alkylation demonstrated to produce exquisite selectivity extending beyond glycosidase inhibition, to immunosuppressant and antibacterial activities.

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ChemInform Abstract: Stereoselective Catalytic Double Osmylation of 1,2‐Dihydropyridines leading to Aminoarabinose and to Aminoaltrose Derivatives and to Potential Glycosidase Inhibitors.

et al. 1994

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Stereoselective Catalytic Double Osmylation of 1,2-Dihydropyridines leading to Aminoarabinose and to Aminoaltrose Derivatives and to Potential Glycosidase Inhibitors.-The title reaction leads, after hydrolysis, to the racemic aza sugars ( IV). In basic medium, the piperidinoses (III) equilibriate with their furanoses (V). One-pot hydrogenolysis and reaction with aldehydes (5 compounds) such as (VI) yield tertiary amines (VII), which show an antiviral activity less than that of the reference substance castanospermine.-(TSCHAMBER, T.; BACKENSTRASS, F.; NEUBURGER, M.; ZEHNDER, M.; STREITH, J.; Tetrahedron 50 (1994) 4, 1135-1152; Lab. Synth.

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Stereoselective catalytic double osmylation of 1,2-dihydropyridines leading to amino-arabinose and to amino-altrose derivatives and to potential glycosidase inhibitors.

Cited by 24 publications

References 17 publications

A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

Biological activities of 3,4,5‐trihydroxypiperidines and their N‐ and O‐derivatives

ChemInform Abstract: Stereoselective Catalytic Double Osmylation of 1,2‐Dihydropyridines leading to Aminoarabinose and to Aminoaltrose Derivatives and to Potential Glycosidase Inhibitors.

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