Efficient and Stereodivergent Syntheses of <scp>D</scp>‐ and <scp>L</scp>‐Fagomines and Their Analogues

Kumari, Nitee; Reddy, Bharat; Vankar, Yashwànt D.

doi:10.1002/ejoc.200800796

Cited by 37 publications

(13 citation statements)

References 67 publications

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“…8e10 For instance, they can be prepared by formation of 2-iodo-2-deoxyglycoside, followed by dehalogenation. 8 Likewise, similar procedures also include the formation of 2-chloro-2-deoxyglycoside and subsequent radical dechlorination, 9 as well as the preparation of 2-deoxy-2-phenylthio-glycoside followed by the reduction of Raney Nickel. 10 Previous reports indicated that acid-catalyzed addition to glycals represents the most direct method that can be operated under various conditions, including hydrogen bromide, 11 triphenylphosphine hydrogenbromide, 12 Dowex-50 [H þ ] in the presence of LiBr, 13 CeCl 3 $7H 2 O/NaI, 14 LaCl 3 $7H 2 O/NaI, 15 TMSOTfeNEt 3 , 16 BCl 3 (or BBr 3 ), 17 ceric ammonium nitrate, 18 GaCl 3 ,19 and Rhenium(V) [ReOCl 3 (SMe 2 )(OPPh 3 )].…”

Section: Introductionmentioning

confidence: 98%

Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

et al. 2011

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Section: Introductionmentioning

confidence: 98%

Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

et al. 2011

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“…In continuation of our interest in synthesizing structurally diverse sugar derivatives as glycosidase inhibitors, we herein wish to report a stereoselective synthesis of an imino glycal. Further, we also report on the utility of the imino glycal in the synthesis of (–)‐1‐ epi ‐adenophorine, and a homoiminosugar and report its glycosidase inhibition activity.…”

Section: Introductionmentioning

confidence: 99%

A Stereoselective Synthesis of an Imino Glycal: Application in the Synthesis of (–)‐1‐epi‐Adenophorine and a Homoimindosugar

et al. 2018

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A concise stereoselective synthesis of an imino glycal is described in 8 steps starting from 1,2‐anhydro‐3,4,6‐tri‐O‐benzyl‐d‐glucopyranose. The utility of the imino glycal has been demonstrated in synthesis of (–)‐1‐epi‐adenophorine and a homoiminosugar as a glycosidase inhibitor. The important features of the developed route include high yields, high stereoselectivity, and application in the synthesis of other iminosugars. Additionally, a new synthon 2‐nitro‐imino glycal has also been synthesized which could act as valuable synthon in carbohydrate chemistry.

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“…For diastereodivergent routes to D-and L-fagomines, with potent antihyperglycemic effect and having potentiation of glucose-induced insulin secretion, 25 a 2-chloroamine obtained from 3,4,6-tri-O-benzyl-D-glucal has been used as common substrate by Vankar and co-workers. 26 The main key features of the synthesis is the cyclization step via a S N 2 reaction in the case of L-()-fagomine, whereas in the other case an intramolecular reductive amination gave the other D-diastereomer (Scheme 16). Using the same divergent routes starting from 3,4,6-tri-O-benzyl-D-galactal, which was transformed into the 2-chloro azasugar, the corresponding L-(+)-and D-(+)-1,2-dideoxy-galactostatins were synthesized as well.…”

Section: Azasugarsmentioning

confidence: 99%

Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes

et al. 2020

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The natural occurrence of enantio-and diastereomers is often encountered. In addition, the synthesis of these stereoisomers is important for structure determination and for the study of structure-activity-relationships. Stereodivergent routes simplify the access to these molecules starting from a common material. This review is focused on the synthesis of carbohydrates, amino acids, alkaloids and terpenes using this efficient strategy. In the case of carbohydrates, such as monosaccharides, carbasugars, aminosugars and azasugars, carbohydrates are usually employed as common starting materials. As a very common strategy, configurations of hydroxy groups are inverted by S N 2 methods playing with protection and deprotection processes. For the synthesis of acyclic α-AAs diastereoselective methods using mainly Garner's aldehyde have been described. Diastereodivergent routes allowed the synthesis of β-hydroxy-and β-amino-α-amino acids, as well as of β-and γ-amino acids. Heterocyclic and cyclic amino phosphonic acids were synthesized using diastereodivergent routes. Alkaloids containing five-and six-membered saturated azaheterocycles needed multistep stereodivergent routes as well as other alkaloids, such as enantiomers of balanol, vincamine, anatoxin and codeine and diastereomeric isochaetominines C and galanthamines. In the terpene field, sesquiterpenes β-santalene, αcurcumene and α-cuparenone and the diterpene scopadulcic acid A were synthesized using enantiodivergent routes. ____________________________________________________________________________

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Efficient and Stereodivergent Syntheses of D‐ and L‐Fagomines and Their Analogues

Abstract: The syntheses of D-and L-fagomines 1, 4, 5 and 6 and their isomers from starting D-glycals have been achieved. The syntheses involve elaboration of common amino alcohol precursors obtained from 2-deoxy-1-amino sugar derivatives. The

Cited by 37 publications

References 67 publications

Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

A Stereoselective Synthesis of an Imino Glycal: Application in the Synthesis of (–)‐1‐epi‐Adenophorine and a Homoimindosugar

Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes

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