The Synthesis of 4-amino-4-deoxy-D-mannose and Glucosamine: A New Methodology for the Design of Homochiral Amino Sugars from non-Carbohydrate Precursors

Pitzer, Kevin K.; Kudlicky, Tomas

doi:10.1055/s-1995-5098

Cited by 24 publications

(8 citation statements)

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“…A similar method has also been used by Hudlicky in a synthesis of a 4-deoxy-4-amino mannose. 115 Epoxide 229 was formed by treatment of the diene 26 with N-bromosuccinimide followed by sodium hydroxide (Scheme 54). Selective allylic epoxide opening with potassium hydroxide and highly selective protection of the least hindered allylic hydroxyl group yielded the dimethylthexylsilyl ether 230.…”

Section: Synthesis Of Amino Sugarsmentioning

confidence: 99%

Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources

et al. 1996

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Section: Synthesis Of Amino Sugarsmentioning

confidence: 99%

Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources

et al. 1996

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“…The regiochemical outcome obtained for the epoxide opening is in agreement with the literature Organic & Biomolecular Chemistry Paper reports for the opening of allylic cyclohexene oxides of type 10 and 6, which takes place exclusively at the allylic position for a number of nucleophiles (alcohols, amines, azides, hydrides, and thiols). [25][26][27][28][29][30][31] The removal of the acetonide group under acidic conditions using CuCl 2 •2H 2 O 22a afforded the diol in 80% yield. Finally, selective mesylation at the allylic position, followed by azide displacement gave 2b in 88% yield for the two-step sequence, representing an overall yield of 27% from cis-diol 1.…”

Section: Preparation Of 14-difunctionalised Monomersmentioning

confidence: 99%

Readily accessible azido-alkyne-functionalized monomers for the synthesis of cyclodextrin analogues using click chemistry

Daher

Seoane

2022

Org. Biomol. Chem.

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“…Some conduramines have significant glycosidase inhibitory activity, but they are of much greater importance as synthetic precursors of amino- and diaminocyclitols, many of which constitute the aglycon portions of the therapeutically useful aminoglycoside antibiotics. In addition, conduramines have been utilized as intermediates in the preparation of azasugars, aminosugars, sphingosines, and narcissus alkaloids . Given the importance of conduramines as synthetic building blocks, it is not surprising that so much effort has been devoted to the development of useful preparative routes to these compounds 3a,e,o,8 and their derivatives. 3d,f-h,j-l,n,− , Hudlicky et al (op.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, conduramines have been utilized as intermediates in the preparation of azasugars, aminosugars, sphingosines, and narcissus alkaloids . Given the importance of conduramines as synthetic building blocks, it is not surprising that so much effort has been devoted to the development of useful preparative routes to these compounds 3a,e,o,8 and their derivatives. 3d,f-h,j-l,n,− , Hudlicky et al (op. cit.)…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Conduramines fromN-tert-Butoxycarbonylpyrrole

Leung-Toung¹,

Liu²,

Muchowski³

et al. 1998

J. Org. Chem.

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Two related synthetic strategies were devised to convert the Diels-Alder adduct 3c of Boc-pyrrole and p-toluenesulfonylacetylene into various racemic and optically pure conduramines. One process consists of the regio-and stereoselective hydroxylation of 3c to the tri-and dihydroxylated azabicyclo-[2.2.1]heptane derivatives 10b (Scheme 2) and the exo-endo mixture 13-14 (Scheme 3). Anionic fragmentation of 10b (methylmagnesium bromide) and of the 13-14 sulfone mixture (lithium bis-(trimethylsilyl)amide) generated the corresponding tri-and dihydroxylated aminocyclohexenes 17 and 16 (Scheme 3). Compound 17 is an aminocyclitol with a stereochemistry and partial aminotriol sequence identical to that found in neoinosamine. Compound 16 served as a source of the protected and free aminodiols 35b and 35a (Scheme 6), which were stereospecifically epoxidized to 36 (Scheme 6) and 40 (Scheme 7). Phenylselenide cleavage of these epoxides provided 37 (Scheme 6) and 41a (Scheme 7), which after selenoxide cycloelimination and protecting group manipulation were converted into (()-conduramine C-1 (39a, Scheme 6) and the previously unreported, all-cisconduramine D-1 (43a, Scheme 7). In a second process, anionic fragmentaion of the bicyclic system is effected prior to introduction of the hydroxyl groups, as exemplified by the high-yielding conversion of the exo-endo mixture of azabicycloheptenes 11 and 12 into the aminocyclohexadiene 15 (Scheme 3). Osmate catalyzed cis-dihydroxylation of the derived bis-Boc derivative 20 (Scheme 4) led stereospecifically to the R-cis-diol 21 which was transformed into (()-conduramine A-1 (27a) and its tetraacetyl derivative 27b via the epoxy compound 24. On the other hand, peracid oxidation of the diene 15 gave the β-epoxide 28 (Scheme 5) which was cleaved to the trans-diol 29 with aqueous sulfuric acid. This diol was converted into (()-conduramine F-1 (34a) and its tetraacetyl derivative (34b) by a reaction sequence similar to that used for the other conduramine syntheses. Fractional crystallization of the diastereomeric mixture of Michael adducts obtained from (()-3c and (-)methyl lactate gave (-)-44a and (-)-45a both in g47% yield (Scheme 8). Both the carboxylic acid (+)-44b and the primary alcohol (+)-46 derived from (-)-44a were converted into (-)-3c with excess methylmagnesium bromide (ca. 40% overall yield). In the same way (-)-45a was transformed into optically pure (+)-3c. (-)-3c and (+)-3c were then converted into (-)-conduramine C-1 [(-)-39a] and (+)-conduramine D-1 [(+)-43a] by procedures identical to those used for the racemic compounds.

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The Synthesis of 4-amino-4-deoxy-D-mannose and Glucosamine: A New Methodology for the Design of Homochiral Amino Sugars from non-Carbohydrate Precursors

Cited by 24 publications

References 0 publications

Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources

Modern Methods of Monosaccharide Synthesis from Non-Carbohydrate Sources

Readily accessible azido-alkyne-functionalized monomers for the synthesis of cyclodextrin analogues using click chemistry

Synthesis of Conduramines fromN-tert-Butoxycarbonylpyrrole

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