Verzweigte zucker, IX

Paulsen, Hans; Eberstein, K.

doi:10.1016/s0040-4039(00)72178-2

Cited by 7 publications

(5 citation statements)

References 6 publications

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“…The 3,4‐epoxide is subsequently opened with benzyl alcohol under acidic conditions, [238] and then converted into the desired 2,3‐epoxide 184 [239–241] . This material is one of the so‐called “Cerny epoxides” and is opened by attack of azide at C‐2 [242] . The resultant azidosugar was alkylated with ( S )‐2‐chloropropionic acid, methylated with diazomethane, and then debenzylated while simultaneously reducing and acetylating the 2‐azide under hydrogenation conditions with added acetic anhydride.…”

Section: Anhydro‐pg Fragmentsmentioning

confidence: 99%

“…[239][240][241] This material is one of the so-called "Cerny epoxides" and is opened by attack of azide at C-2. [242] The resultant azidosugar was alkylated with (S)-2chloropropionic acid, methylated with diazomethane, and then debenzylated while simultaneously reducing and acetylating the 2-azide under hydrogenation conditions with added acetic anhydride. The resulting methyl ester of 1,6-anhydro-MurNAc 185 served as the glycosyl acceptor for 3,4,6-tri-O-acetyl-2-Nphthalimido-D-glucosaminyl bromide under Koenigs-Knorr conditions.…”

Section: Anhydro-pg Fragmentsmentioning

confidence: 99%

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Recent Advances in the Synthesis and Biological Applications of Peptidoglycan Fragments

Vacariu

Tanner

2022

Chemistry A European J

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The biosynthesis, breakdown, and modification of peptidoglycan (PG) play vital roles in both bacterial viability and in the response of human physiology to bacterial infection. Studies on PG biochemistry are hampered by the fact that PG is an inhomogeneous insoluble macromolecule. Chemical synthesis is therefore an important means to obtain PG fragments that may serve as enzyme substrates and elicitors of the human immune response. This review outlines the recent advances in the synthesis and biochemical studies of PG fragments, PG biosynthetic intermediates (such as Park's nucleotides and PG lipids), and PG breakdown products (such as muramyl dipeptides and anhydro‐muramic acid‐containing fragments). A rich variety of synthetic approaches has been applied to preparing such compounds since carbohydrate, peptide, and phospholipid chemical methodologies must all be applied.

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Section: Anhydro‐pg Fragmentsmentioning

confidence: 99%

Section: Anhydro-pg Fragmentsmentioning

confidence: 99%

Recent Advances in the Synthesis and Biological Applications of Peptidoglycan Fragments

Vacariu

Tanner

2022

Chemistry A European J

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“…Thus the known epoxy uloside 3 seemed to be a plausible intermediate. Paulsen and Eberstein had shown that methyllithium addition to 3 gave virtually equal amounts of 4 and 6 ( 13). W e decided to examine the hydration of the exoCan.…”

Section: Introductionmentioning

confidence: 99%

Stereocontrolled routes to cis-hydroxyamino sugars. Part VI. A synthesis of garosamine

Pauls¹,

Fraser‐Reid²

1984

Can. J. Chem.

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. Can. J. Chem. 62, 1532Chem. 62, (1984. The exocyclic olefin, 5, obtained from the known epoxy uloside, methyl 2.3-anhydro-P-D-erythro-pentopyranosid-4-ulose, 3, reacts with ammonia or methylamine to give the 3-amino-3-deoxy or 3-methylamino-3-deoxy derivatives respectively. The benzamide, 8c, obtained from the former, reacts with iodonium ion to give an oxazoline in which the cis relationship between the tertiary alcohol and the 3-amino group of garosamine is secured. Deiodination is followed by a one-pot N-methylation and reduction. A hydrolysis gives methyl a-L-garosamimide 2. In a second route, the urethane, 16c, reacts with iodonium ion to give an oxazolidone 170. This reaction establishes the cis-hydroxyamino moiety and circumvents the N-methylation/reduction steps. Deiodination followed by deprotection yields methyl a-L-garosaminide 2. Both routes require eight steps from 3 with overall yields of 14% and I I %, respectively. HENRY W. PAULS et BERT FRASER-REID. Can. J. Chem. 62, 1532Chem. 62, (1984 L'olCfine exocyclique, 5, qui est obtenue de I'Cpoxy uloside connu, anhydro-2,3 P-D-Prythro-pentopyrannoside ulose-4 de mCthyle, 3, rCagit avec I'ammoniac ou la mCthylamine pour donner, suivant le cas, soit le dCrivC amino-3 dCoxy-3 ou methylamino-3 dCoxy-3. Le benzamide 8c, obtenu a partir du premier de ces dCrivts, rCagit avec I'ion iodonium pour donner une oxazoline dans laquelle on a fixC, entre I'alcool tertiaire et le groupe amino-3, la relation cis qui existe dans la garosamine. Aprks 1'Climination de I'iode. on effectue, dans le meme ballon, une N-mtthylation suivie d'une rCduction. Une hydrolyse conduit a la a-L-garosamimide de mCthyle, 2. Dans une deuxikme voie de synthkse, on fait rCagir I'urCthane 16c avec I'ion iodonium pour obtenir une oxazolidone 170. Cette rCaction permet d'Ctablir la relation cis de la portion amino-alcool et Cvite les Ctapes de N-mCthylation/rCduction. L'Climination de I'iode, suivie d'une deprotection, conduit au produit 2. Chacune des voies requiert huit Ctapes a partir du produit 3 et leurs rendements respectifs sont de 14% et 11%.[Traduit par le journal]

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“…The desulfuration product (3) obtained from (2) undergoes selective reaction in the side chain with LiAlH4 but not in the epoxide ring, thus yielding ( 4 ) and (5). Hydrolysis of ( 5 ) likewise furnishes (10).…”

mentioning

confidence: 99%

“…It is important that acidic methanolysis of ( 5 ) leads via the equilibrium ( 5 ) % ( 1 0 ) + ( 9 ) to an isomerization of ( 5 ) to ( 9 ) (a,P form); ( 9 ) is considerably more stable than (5). Accordingly, no information about the stereochemistry at the branching point of the octose is available from hydrolysis of the quinocycline complex.…”

mentioning

confidence: 99%

CC Linkage of Polyfunctional Molecules by Nucleophilic Addition of Dianions. Synthesis of Pillarose

Paulsen

Roden

Sinnwell

et al. 1976

Angew. Chem. Int. Ed. Engl.

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Verzweigte zucker, IX

Cited by 7 publications

References 6 publications

Recent Advances in the Synthesis and Biological Applications of Peptidoglycan Fragments

Recent Advances in the Synthesis and Biological Applications of Peptidoglycan Fragments

Stereocontrolled routes to cis-hydroxyamino sugars. Part VI. A synthesis of garosamine

CC Linkage of Polyfunctional Molecules by Nucleophilic Addition of Dianions. Synthesis of Pillarose

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