Dérivés C-glycosyliques

Tronchet, J. M. J.; Barbalat-Rey, Françoise; Le‐Hong, Nghiep; Bürger, Ulrich

doi:10.1016/s0008-6215(00)83016-5

Cited by 21 publications

(15 citation statements)

References 45 publications

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“…Oxidation 18 of 19 with lead tetraacetate afforded the desired aldehyde 20 in excellent yield (97%), that was converted into the corresponding oxime 21 (yield: 60%, mixture of syn and anti stereoisomers). 7 Chlorination at -30 °C in DCM solution of 21 gave the desired hydroxymoyl chloride 22 in 74% yield. 19 All the structures of the above reported products were confirmed by spectroscopic analyses and found to be identical with reported data.…”

Section: Scheme 6 Synthesis Of Thementioning

confidence: 99%

“…All the reported synthetic steps are well described in literature. 7 D-Mannitol (9) is protected through reaction with 2,2dimethoxypropane in the presence of SnCl 2 as the catalyst to afford the compound 10 in 60% yield. 8 Oxidation of the diol 10 with periodate led to the aldehyde 11 in 63% yield.…”

Section: Paper Synthesismentioning

confidence: 99%

“…Compounds 10-13 were prepared according the established procedures, [7][8][9] and their structures were confirmed by comparison with the reported spectroscopic data. Analogously, compounds 18-22 were prepared according the established procedures, [17][18][19] and their structures were confirmed by comparison with the reported spectroscopic data.…”

Section: Paper Synthesismentioning

confidence: 99%

“…9 The structures of all the products reported in Scheme 3 were confirmed by spectroscopic analyses and found identical with the characterizations reported in cited literature. [7][8][9] The first attempts to generate in situ the nitrosocarbonyl intermediate 13NC from the chloroxime 13 were conducted in the presence of freshly distilled cyclopentadiene or 1,3-cyclohexadiene in HDA cycloadditions. Following the previous and well-established protocol, 10 a DCM solution of 13 was added to a solution of 1.2 equivalents of NMO along with 1.1 equivalents of Et 3 N in the presence of 1.5 equivalents of the selected diene in the same anhydrous solvent (Scheme 4).…”

Section: Scheme 1 Synthetic Utility Of Nitrosocarbonyl Chemistry In Hmentioning

confidence: 99%

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Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Corti

Leusciatti²,

Moiola³

et al. 2020

Synthesis

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The generation and trapping of two new nitrosocarbonyl intermediates bearing carbohydrate-based chiral substituents is achieved by the mild oxidation of the corresponding nitrile oxides with tertiary amine N-oxides. Their capture with suitable dienes and alkenes afforded the corresponding hetero Diels–Alder cycloadducts and ene adducts from fair to excellent yields. The entire methodology looks highly promising by the easy conversion of aldoximes into hydroxymoyl halides, widening the access to nitrosocarbonyls, versatile tools in organic synthesis.

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Section: Scheme 6 Synthesis Of Thementioning

confidence: 99%

Section: Paper Synthesismentioning

confidence: 99%

Section: Paper Synthesismentioning

confidence: 99%

Section: Scheme 1 Synthetic Utility Of Nitrosocarbonyl Chemistry In Hmentioning

confidence: 99%

See 2 more Smart Citations

Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Corti

Leusciatti²,

Moiola³

et al. 2020

Synthesis

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“…The signal of H-C(2) appears at 5.34 ppm for the major diastereoisomer and at 5.56 ppm for the minor diastereoisomer. In the (E)-diastereoisomer, H-C(2) is closer to the N-phosphate group, and its signal is found at lower field than the one of H-C(2) of (Z)-8 [29]. The structure of 9 was established by X-ray analysis (Figure) ').…”

mentioning

confidence: 99%

Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

Meuwly

Vasella

1985

Helvetica Chimica Acta

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Treatment of the chloro-nitro-ribofuranose 7 with KPO(OMe)2 gave the 0-amino phosphate 8 (5%) and the nitrile 9 (62%). Compound 9 was also obtained by the reaction of 8 with KPO(OMe),, and its structure was established by X-ray analysis. Treatment of the chloro-nitro-mannofuranose 10, the bromo-nitro-ribofuranose 14, or the bromo-nitro-mannofuranose 16, respectively, with the K or Na salt of HPO(OMe)2 lead also to 0-amino phosphates and nitriles. The (1-C-nitrog1ycosyl)phosphonate 22 was obtained (21 %) together with the nitrile 21 (5 1 %) from the chloro-nitro-mannofuranose 10 and KPO(OEt)2. The reaction of the I-C-nitroglycosyl sulfone 25 (NO2-group endo) with KPO(OEt), gave the (I-C-nitroglycosy1)phosphonate 22 (61 %) and the nitrile 21 (1 1 YO), whilst the anomeric sulfone 26 (NO,-group exo) gave 22 (15%) and 21 (58%). In the presence of [18]crown-6, a mixture of the anomers 25 and 26 gave the (I-C-nitroglycosy1)phosphonate 22 in 67% yield together with 21 (13%). These findings are rationalized as the result of a competition between a nucleophilic attack of the dialkyl-phosphite anions on the NO2-group leading ultimately to the nitrile 21 and a single-electron transfer reaction leading to the (1-C-nitroglycosy1)phosphonate 22.

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Synthesis of Glycosidase‐Inhibiting Iminopolyols Via Isoxazolines^1,2

Jäger

Müller

Leibold

et al. 1994

Bulletin des Soc Chimique

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The 1 ,3-dipolar cycloaddition of ally1 halides with chiral nitrile oxides, derived from glyceraldehyde derivatives, affords ca. 1 :1-mixtures of C5-epimeric isoxazolines. The diastereomers can be separated on a preparative scale by MPLC; the configurations at C5 are established by chemical correlation/>(-ray analysis initially, and then routinely, based on consistent, large differences of respective specific rotations. -An unexpected finding, which turned out to be the key to efficient transformation of 5-halomethyl-isoxazolines into hydroxy-pyrrolidines, is that highly stereoselective catalytic hydrogenations are feasible with proper combination of both 3-and 5-side chain structures and the catalyst system. -This (CJ + Cd-approach is extended to include dihydroxy-pyrrolidines, i. 8.

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Dérivés C-glycosyliques

Cited by 21 publications

References 45 publications

Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

Synthesis of Glycosidase‐Inhibiting Iminopolyols Via Isoxazolines^1,2

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Dérivés C-glycosyliques

Cited by 21 publications

References 45 publications

Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Deoxy‐nitrosugars. 11th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

Synthesis of Glycosidase‐Inhibiting Iminopolyols Via Isoxazolines1,2

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Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

Synthesis of Glycosidase‐Inhibiting Iminopolyols Via Isoxazolines^1,2