First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

Gurjar, Mukund K.; Nagaprasad, Ravi; Ramana, Chepuri V.

doi:10.1016/s0040-4039(02)01760-4

Cited by 24 publications

(13 citation statements)

References 19 publications

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“…The coupling reaction between 55 and 56 gave diasteromeric mixture 57, which was subjected to three subsequent steps, i.e. dehydration, selective reduction of conjugated olefin and denitration, to give the penta-O-benzyl C-disaccharide 59 (Scheme 13) [20].…”

Section: Nitro Stabilized Anionsmentioning

confidence: 99%

Recent Advances in the Synthesis of C-oligosaccharides

Yuan

Linhardt²

2005

CTMC

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This paper reviews the recent advances in the synthesis of catabolically stable sugar mimetics, Coligosaccharides. These compounds are synthetic analogs of the naturally occurring Ooligosaccharides, in which the interglycosidic oxygen has been replaced by a methylene group. This review is organized in terms of chemistry used to assemble C-oligosaccarides under the subheadings: anionic approaches, cationic methods, reductive glycosyl samarium chemistry, cyclization methodology, and free radical chemistry.

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Section: Nitro Stabilized Anionsmentioning

confidence: 99%

Recent Advances in the Synthesis of C-oligosaccharides

Yuan

Linhardt²

2005

CTMC

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“…Previous syntheses of this C-disaccharide have been described; they have involved a nitro-aldol condensation reaction, [10] a Wittig reaction, [11] or the addition of an alkynyl anion to a sugar lactone. The main control element of the reaction is the substituent on the 4-position or the starting furanosyl sulfone.…”

mentioning

confidence: 99%

“…Previous syntheses of this C-disaccharide have been described; they have involved a nitro-aldol condensation reaction, [10] a Wittig reaction, [11] or the addition of an alkynyl anion to a sugar lactone. Previous syntheses of this C-disaccharide have been described; they have involved a nitro-aldol condensation reaction, [10] a Wittig reaction, [11] or the addition of an alkynyl anion to a sugar lactone.…”

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confidence: 99%

Samarium Diiodide Mediated Coupling of 2‐Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C‐Furanosides

2015

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Diiodosamarium‐mediated coupling of anomeric 2‐pyridyl sulfones derived from furanosides with carbonyl compounds, aldehydes, and ketones gave α‐hydroxylated 2,5‐trans‐dialkylated tetrahydrofurans with good yields and useful stereoselectivities. The main control element of the reaction is the substituent on the 4‐position or the starting furanosyl sulfone. C‐Furanosides of D‐arabinose and of D‐ribose were obtained from sulfones prepared from the corresponding furanosides. Finally, a di‐C‐arabinofuranoside, a C‐disaccharide analogue of a major motif of the arabinogalactan from the mycobacterial cell wall, was prepared.

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“…27 Thus, zinc mediated reductive opening on the 5-deoxy-5-iodo- d -arabinofuranoside 16 afforded enal 17 . 28 , 29 Treatment of 17 with methyl(triphenylphosphoranylidene)acetate provided 18 as a single E -isomer. Selective hydrogenation of the conjugated alkene followed by hydrolysis of the ester led to 19 .…”

Section: Resultsmentioning

confidence: 99%

A ring closing metathesis strategy for carbapyranosides of xylose and arabinose

Mattis

Mootoo

2016

Carbohydrate Research

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The synthesis of β-carba- xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether-alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration-oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.

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First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

Cited by 24 publications

References 19 publications

Recent Advances in the Synthesis of C-oligosaccharides

Recent Advances in the Synthesis of C-oligosaccharides

Samarium Diiodide Mediated Coupling of 2‐Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C‐Furanosides

A ring closing metathesis strategy for carbapyranosides of xylose and arabinose

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