Pseudo‐sugars, 30. Synthesis of Amino‐5a‐carba‐deoxyhexopyranoses from 2(3)‐Acetoxy‐5‐acetoxymethyl‐3(2)‐<i>p</i>‐toluenesulfonamido‐7‐oxabicyclo[2.2.1]heptanes

Ogawa, Seiichiro; Tsunoda, Hidetoshi; Yoshikawa, Masae; Uemura, M.; Orihara, Masaru

doi:10.1002/jlac.1992199201108

Cited by 5 publications

(1 citation statement)

References 15 publications

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“…Since then, dl -valienamine, 102b,− dl -hydroxyvalidamine, dl -valiolamine, 2-amino-5a-carbadeoxy- dl -pyranoses, , 3-amino-5a-deoxy- dl -pyranoses, dl -hydroxyvalidamine, dl -1-epi-validamine,102a dl -2-epi-validamine,261b dl -2-amino-2-deoxyvalidamine having α- and β-gluco and α- and β-manno configurations, 5a-carba-α- dl -fucopyranosylamine,114a 5a-carba-α- dl -galactopyranosylamine,114a and fucose-type α- and β-valienamine derivatives, all in racemic form, have also been synthesized using Diels−Alder adduct 576 as starting material.…”

Section: 2 Synthesis Of Carbapyranoses621 Synthesis From Non-carbohyd...mentioning

confidence: 99%

Synthesis and Conformational and Biological Aspects of Carbasugars

et al. 2007

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Section: 2 Synthesis Of Carbapyranoses621 Synthesis From Non-carbohyd...mentioning

confidence: 99%

Synthesis and Conformational and Biological Aspects of Carbasugars

et al. 2007

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ChemInform Abstract: Pseudo‐Sugars. Part 30. Synthesis of Amino‐5a‐carba‐deoxyhexopyranoses from 2(3)‐Acetoxy‐5‐acetoxymethyl‐3(2)‐p‐toluenesulfonamido‐7‐ oxabicyclo(2.2.1)heptanes.

et al. 1992

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Pseudo-Sugars.Part 30. Synthesis of Amino-5a-carbadeoxyhexopyranoses from 2(3)-Acetoxy-5-acetoxymethyl-3(2)p-toluenesulfonamido-7-oxabicyclo(2.2.1)heptanes.-cis-Hydroxyamination of unsaturated endo-acetate (I) under Sharpless conditions followed by acetylation of the positional isomers formed yields the acetates (IV) and (V). Cleavage of their 1,4-anhydro ring with HBr affords bromodeoxycyclitol derivatives which can be easily converted to the target amino-hexopyranoses (cf. (IX), (X)). Applying a similar sequence of reactions to the exo-acetate (XI) offers a convenient approach to the novel talopyranose tetraacetate (XII). -(OGAWA, S.; TSUNODA, H.; YOSHIKAWA, M.; UEMURA, M.; ORIHARA, M.; Liebigs Ann. Chem. (1992) 6, 629-636; Dep. Appl. Chem., Fac. Sci.

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Pseudosugars, 32. – Synthesis of 1,4‐Imino‐linked Carbadisaccharides Composed of a 2‐Amino‐5a‐carba‐2‐deoxyglucopyranosylamine Residue and Its Congeners

Ogawa

Tsunoda

1993

Liebigs Ann. Chem.

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Carbadisaccharide 5, containing a 2-acetamido-5a-carba-2-deoxyhexopyranosylamine residue, was synthesized by coupling of methyl 4-amino-4-deoxy-a-D-glucopyranoside (41) with the N-(2,4-dinitrophenyl)epimino compound 16 followed by deprotection. The 6'-acetamido-6'-deoxy analog 3 of a potent a-glucosidase inhibitor methyl acarviosin (1) was synthesized from a condensate 50 obtained by coupling of 41 with the protected epimino compound 18, possessing an exomethylene function. This process involves a sequence of reactions: replacement by a benzoate ion and successive dehydrobromination of the dibromide 52 obtained from 50. Hydroxymercuration of 50 followed by demetalation and deprotecThe carbocyclic analog of hexopyranoses, Sa-carbahexopyranosesL21 were found in biologically active substances: antibiotic validamycin~[~] and a-glucosidase inhibitorsL4I, in which they are linked to the sugar or the cyclitol moiety via an imino function, namely a ,,pseudo-N-glycosidic linkage". In order to elucidate the structure-inhibitory activity relationship of the inhibitors of this kind, we have so far synthesized several of methyl acarviosinL61 (1) and its 1 '-epimerL71 2, and carried out their biological assay with some sugar hydrolases.In continuation of our research program, we were interested in preparing carbaoligosaccharides[81 related to the common core structures of the oligosaccharides occurring in cell-surface glycans [']. Since 2-acetamido-2-deoxy-Dhexopyranoses having mainly galacto and gluco configurations are important components of such oligosaccharide structures, we first attempted to prepare versatile precursors 16 and 18 of 2-acetamido-5a-carba-2-deoxyglucopyranosylamine, which may be introduced into the oligosaccharide chains as an imino-linked carbasugar residue instead of that of the true sugar congener. In this paper are described first the preparation of the 5a-carba-1,2-dideoxy-1,2-epiminohexopyranose derivatives 15, 16, 17, and 18 and their transformation into useful precursors of amino-5a-carbadeoxyhexopyranosylamines by substitution reaction with an azide ion. tion gave two carbadisaccharide analogs 3 and 9 containing the valiolamine-type branched aminocyclitol moieties. The free amines 4, 6, 8, and 10 were prepared by treatment of the corresponding N-protected derivatives with Amberlite IRA 400 (OH-) resin. Biological assays of all carbadisaccharides were carried out with three sugar hydrolases. Only compounds 6 and 8 were shown to be very weak a-mannosidase inhibitors. The introduction of the acetamido or amino function instead of the hydroxyl group into the C-6' position of the methyl acarviosin analog 2 resulted in an appreciable decrease of the inhibitory activity.

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Pseudo‐sugars, 30. Synthesis of Amino‐5a‐carba‐deoxyhexopyranoses from 2(3)‐Acetoxy‐5‐acetoxymethyl‐3(2)‐p‐toluenesulfonamido‐7‐oxabicyclo[2.2.1]heptanes

Cited by 5 publications

References 15 publications

Synthesis and Conformational and Biological Aspects of Carbasugars

Synthesis and Conformational and Biological Aspects of Carbasugars

ChemInform Abstract: Pseudo‐Sugars. Part 30. Synthesis of Amino‐5a‐carba‐deoxyhexopyranoses from 2(3)‐Acetoxy‐5‐acetoxymethyl‐3(2)‐p‐toluenesulfonamido‐7‐ oxabicyclo(2.2.1)heptanes.

Pseudosugars, 32. – Synthesis of 1,4‐Imino‐linked Carbadisaccharides Composed of a 2‐Amino‐5a‐carba‐2‐deoxyglucopyranosylamine Residue and Its Congeners

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