Novel Selectivity in Carbohydrate Reactions, IV: DABCO-Mediated Regioselective Primary Hydroxyl Protection of Carbohydrates

Gadakh, Bharat; Patil, Premanand Ramrao; Malik, Satish; Kartha, K. P. Ravindranathan

doi:10.1080/00397910802656067

Cited by 19 publications

(12 citation statements)

References 7 publications

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“…Analytically pure samples were obtained by either recrystallization or by chromatography on a column of silica. Compounds 6, 11 8, 11 10, 11 12, 11 14, 20 16, 21 20, 18 22, 22 26, 23 28, 24 30, 25 32, 26 34, 26 36, 27 38, 18 40, 26 42, 28 showed complete consumption of the sugar. The solution had become hot due to the exothermic nature of the reaction.…”

Section: General Procedures For the Acetylation Reaction In The Presenmentioning

confidence: 99%

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

2017

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Section: General Procedures For the Acetylation Reaction In The Presenmentioning

confidence: 99%

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

2017

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“…6−8 Modification of the primary hydroxyl group is relatively straightforward by reacting the glycoside with bulky reagents. 9,10 …”

Section: Introductionmentioning

confidence: 99%

“…Activating agents, such as 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and 2-chloro-4,6-dimethoxy-1,3,5-triazine, react selectively with the anomeric hydroxyl group of monosaccharides and oligosaccharides. Sequential nucleophilic substitution with azide, alcohols, and thiols readily converts the resulting reactive intermediates to glycosyl azides, glycosides, and thioglycosides. − Modification of the primary hydroxyl group is relatively straightforward by reacting the glycoside with bulky reagents. , …”

Section: Introductionmentioning

confidence: 99%

“…6−8 Modification of the primary hydroxyl group is relatively straightforward by reacting the glycoside with bulky reagents. 9,10 Methods to selectively functionalize one of the secondary hydroxyl groups are still limited. 11−13 Current research mainly focuses on regioselective acylation and silylation, which is an approach that has been applied in an elegant way in the total synthesis of the ellagitannins, glucoside esters of gallic acid, and hexahydroxy phenoic acid, by the Kawabata group, 14,15 and these regioselective acylation/silylation methods have been thoroughly reviewed recently.…”

Section: ■ Introductionmentioning

confidence: 99%

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Regioselective Carbohydrate Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and Side-Product Formation

2017

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Palladium/neocuproine catalyzed oxidation of glucosides shows an excellent selectivity for the C3-OH, but in mannosides and galactosides, unselective oxidation was initially observed. For further application in more-complex (oligo)saccharides, a better understanding of the reaction, in terms of selectivity and reactivity, is required. Therefore, a panel of different glycosides was synthesized, subjected to palladium/neocuproine catalyzed oxidation and subsequently analyzed by qNMR. Surprisingly, all studied glucosides, mannosides, galactosides, and xylosides show selective oxidation of the C3-OH. However, subsequent reaction of the resulting ketone moiety is the main culprit for side product formation. Measures are reported to suppress these side reactions. The observed differences in reaction rate, glucosides being the most rapidly oxidized, may be exploited for the selective oxidation of complex oligosaccharides.

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“…This method eliminates the need for the use of hazardous solvents such as pyridine and DMF for such reactions (Scheme 4) [7].…”

Section: Protection Of Carbohydratesmentioning

confidence: 99%

1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis

Baghernejad

2010

Eur. J. Chem.

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KEYWORDS1,4-diazabicyclo[2.2.2]octane (DABCO) has been used in many organic preparations as a good solid catalyst. DABCO has received considerable attention as an inexpensive, ecofriendly, high reactive, easy to handle and non-toxic base catalyst for various organic transformations, affording the corresponding products in excellent yields with high selectivity. In this review, some applications of this catalyst in organic reactions were discussed.

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Novel Selectivity in Carbohydrate Reactions, IV: DABCO-Mediated Regioselective Primary Hydroxyl Protection of Carbohydrates

Cited by 19 publications

References 7 publications

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

Regioselective Carbohydrate Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and Side-Product Formation

1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis

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