Cyclic Monosaccharides Having Nitrogen or Sulfur in the Ring

Paulsen, Hans; Todt, Klaus

doi:10.1016/s0096-5332(08)60169-1

Cited by 83 publications

(24 citation statements)

References 151 publications

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“…Die Umsetzung mit Chlorameisensaure-benzylester 19,20) sowie an N-substituierten 2-Alkylpiperidin-Derivaten2') gut untersucht worden. Er wird auch dort beobachtet und steht mit den konformativen Beobachtungen an 4 in guter Ubereinstimmung.…”

unclassified

Monosaccharide mit Stickstoff im Ring, XXXIX. Synthese von modifizierten α‐L‐Fucosidase‐Inhibitoren, die 1,5‐Didesoxy‐1,5‐imino‐L‐fucit als Basisstruktur enthalten

et al. 1990

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Monosaccharides Containing Nitrogen in the Ring, XXXIX'). Inhibitors of a-L-FucosidaseVariation of the side chain in the 1,3-dithiane derivative 1 of D-galactose leads to a series of analogues of 1,5-dideoxy-1,5-imino-L-fucitol (deoxyfuconojirimycin) (33), which are potent inhibitors of a-L-fucosidase. Cleavage of the dithioacetal in 5 followed by reduction of the aldehyde 6 and deblocking results in 1,5-dideoxy-l,5-imino-~-galactito1 (8). The aldehyde 6 is converted by Wittig reaction to 10 and 14 via 9 and 13, which are homologues of 1,5-dideoxy-l,5-imino-~-fucitol (33). Cyclization of the Wittig product 15 yields the y-lactam 18. After

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unclassified

Monosaccharide mit Stickstoff im Ring, XXXIX. Synthese von modifizierten α‐L‐Fucosidase‐Inhibitoren, die 1,5‐Didesoxy‐1,5‐imino‐L‐fucit als Basisstruktur enthalten

et al. 1990

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“…The debenzylidenated nitro sugar 4 was converted by sulfonylation into the 6-0-p-toluenesulfonate 6. The latter readily condensed with acetone to yield methyl 2-deoxy-3,4-O-isopropylidene-3-C-nitromethyl-6-ptolylsulfonyl-a-D-ribo-hexopyranoside (11). This evidence confirms the presence of a cis glycol at C-3 and -4, and therefore compound 4 is undoubtedly methyl 2-deoxy-3-C-nitromethyl-a-Dribo-hexopyranoside.…”

mentioning

confidence: 66%

Branched-chain aminodeoxy sugars. Methyl 3-C-aminomethyl-2-deoxy-α-D-ribo-hexopyranoside and methyl 3-C-aminomethyl-2-deoxy-α-D-arabino hexopyranoside

Rosenthal¹,

Ong²

1970

Can. J. Chem.

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Addition of methyl 4,6-O-benzylidene-2-deoxy-a-~-e,.ythro-hexopyranosid-3-ulose (1) to excess nitromethane and 1 molar equivalent of sodium methoxide in methanol gave methyl 4,6-0-benzylidene-2-deoxy-3-C-nitromethyl-a-D-ribo-hexopyranode (2) and the arabino stereoisomer 3 in 63 and 22% yields, respectively. The proof of structure of the branched-chain deoxy nitro sugars is described. Debenzylidenation of the nitro sugars afforded the partially blocked nitro sugars 4 and 5. Catalytic hydrogenation of the latter or of 2 and 3 yielded the branched-chain aminodeoxy sugars 7 and 9 (7 characterized as its N-acetyl derivative and 9 as its N-2,4-dinitrophenyl derivative).

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“…Paulsen and Todt have prepared a large number of piperidine aminosugars whose ring N-atoms were acylated [14]: in all instances the C(l) substituent proved to be axial (a-anomers in the D-series). According to these authors, the anomeric effect is much stronger in the piperidine-sugar series than in the pyranose-sugar series [ 141 [ 151.…”

Section: Relative Configurations and Major Conformationsmentioning

confidence: 99%

Syntheses of Racemic Diaminosugar Derivatives Starting from 1,2‐Dihydropyridines and from Nitrosobenzene

Augelmann

Streith

Fritz

1985

Helvetica Chimica Acta

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Racemic diaminosugars were easily obtained by a regio-and stereoselective three-step synthetis. In the first step, regiospecific hetero-Diels-Alder cycloadditions between 1,2-dihydropyridines l a and 10 and nitrosobenzene led to the bicyclic compounds 2a and 11, respectively. cis-Glycol formation starting from these latter adducts, followed by hydrogenolysis of the N -0 bond and by exhaustive acetylation of the OH-groups, led to the diaminolyxose 5, the diaminomannose 14 and the diaminoallose 15. When starting from benzyl 1,2-dihydropyridine-1-carboxylate (lb) and using the same reaction sequence, the racemic piperidine derivative 8 was obtained.Racemic 4,5-Diamino-4,5-dideoxy-lyxopyranose 4. -In a preliminary paper, we described a simple three-step synthesis of the racemic diamino-dideoxy-lyxopyranose [l] which is represented in formula 4 by its cc-D-enantiomer. The reaction sequence was straightforward: i) regiospecific Diels-Alder cycloaddition of dihydropyridine l a with

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Cyclic Monosaccharides Having Nitrogen or Sulfur in the Ring

Cited by 83 publications

References 151 publications

Monosaccharide mit Stickstoff im Ring, XXXIX. Synthese von modifizierten α‐L‐Fucosidase‐Inhibitoren, die 1,5‐Didesoxy‐1,5‐imino‐L‐fucit als Basisstruktur enthalten

Monosaccharide mit Stickstoff im Ring, XXXIX. Synthese von modifizierten α‐L‐Fucosidase‐Inhibitoren, die 1,5‐Didesoxy‐1,5‐imino‐L‐fucit als Basisstruktur enthalten

Branched-chain aminodeoxy sugars. Methyl 3-C-aminomethyl-2-deoxy-α-D-ribo-hexopyranoside and methyl 3-C-aminomethyl-2-deoxy-α-D-arabino hexopyranoside

Syntheses of Racemic Diaminosugar Derivatives Starting from 1,2‐Dihydropyridines and from Nitrosobenzene

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