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Search for "anomeric stereoselectivity" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

Kesatebrhan Haile Asressu and
Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

, De Meo and co-workers have reported the significant effect of O-substituents on atom C-7 on the reactivity of thiosialoside donors and on the anomeric stereoselectivity of chemical sialylations [21]. Thus, 2,7-anhydro-Neu5Ac can serve as a promising building block for the chemical synthesis of

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Figure 1: Representative structures of bacterial glycans containing sialic acid.

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Scheme 1: Concise synthesis of 2,7-anhydrosialic acid derivatives 2–6. Conditions for the preparation of 2 an...

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Figure 2: a) ORTEP diagram of compound 4. Thermal ellipsoids indicate 50% probability. b) HMBC spectrum of 6.

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Scheme 2: N- and C-1-functionalization of 2.

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Scheme 3: Mechanism of the SnCl₄-catalyzed acetolysis of 2,7-anhydro derivatives 15. R = Me, Bn, PG = electro...

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Scheme 4: Synthesis and acetolysis of 2,7-anhydro derivatives 21 and 25.

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Figure 3: HMBC spectrum of carbohydrate 22.

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Scheme 5: Attempted acetolysis of 2,7-anhydro-NeuN₃-based disaccharides 29, 33, and 37.

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Published 23 Dec 2019

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Anomeric modification of carbohydrates using the Mitsunobu reaction

Julia Hain,
Patrick Rollin,
Werner Klaffke and
Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

circumstances. Keywords: anomeric stereoselectivity; carbohydrates; glycoside synthesis; Mitsunobu reaction; Introduction Fifty years ago, Oyo Mitsunobu reported a preparation of esters from alcohols and carboxylic acids supported by two auxiliary reagents, diethyl azodicarboxylate (DEAD) and

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Scheme 1: Left: The Mitsunobu reaction is essentially a nucleophilic substitution of alcohols occurring with ...

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Scheme 2: Mechanistic considerations on the Mitsunobu reaction with carbohydrate hemiacetals (depicted in sim...

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Scheme 3: Anomeric esterification using the Mitsunobu procedure [29].

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Scheme 4: Conversion of allyl glucuronate into various 1-O-esterified allyl glucuronates using anomeric Mitsu...

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Scheme 5: Synthesis of anomeric glycosyl esters as substrates for Au-catalyzed glycosylation [40].

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Scheme 6: Correlation between pK_a value of the employed acids (or alcohol) and the favoured anomeric configur...

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Scheme 7: Synthesis of the β-mannosyl phosphates for the synthesis of HBP 43 by anomeric phosphorylation acco...

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Scheme 8: Synthesis of phenyl glycosides 44 and 45 from unprotected sugars [24].

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Scheme 9: Synthesis of azobenzene mannosides 47 and 48 without protecting group chemistry [46].

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Scheme 10: Synthesis of various aryl sialosides using Mitsunobu glycosylation [25].

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Scheme 11: Mitsunobu synthesis of different jadomycins [54,55]. BOM: benzyloxymethyl.

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Scheme 12: Stereoselectivity in the Mitsunobu synthesis of catechol glycosides in the gluco- and manno-series [56]....

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Scheme 13: Formation of a 1,2-cis glycoside 80 assisted by steric hindrance of the β-face of the disaccharide ...

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Scheme 14: Stereoselective β-D-mannoside synthesis [60].

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Scheme 15: TIPS-assisted synthesis of 1,2-cis arabinofuranosides [63]. TIPS: triisopropylsilyl.

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Scheme 16: The Mitsunobu reaction with glycals leads to interesting rearrangement products [69].

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Scheme 17: Synthesis of disaccharides using mercury(II) bromide as co-activator in the Mitsunobu reaction [75].

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Scheme 18: Synthesis of various fructofuranosides according to Mitsunobu and proposed neighbouring group parti...

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Scheme 19: The Mitsunobu reaction allows stereoslective acetalization of dihydroartemisinin [77].

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Scheme 20: Synthesis of alkyl thioglycosides by Mitsunobu reaction [81].

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Scheme 21: Preparation of iminoglycosylphthalimide 115 from 114 [85].

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Scheme 22: Mitsunobu reaction as a key step in the total synthesis of aurantoside G [87].

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Scheme 23: Utilization of an N–H acid in the Mitsunobu reaction [88].

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Scheme 24: Mitsunobu reaction with 1H-tetrazole [89].

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Scheme 25: Formation of a rebeccamycin analogue using the Mitsunobu reaction [101].

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Scheme 26: Synthesis of carbohydrates with an alkoxyamine bond [114].

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Scheme 27: Synthesis of glycosyl fluorides and glycosyl azides according to Mitsunobu [118,119].

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Scheme 28: Anomeric oxidation under Mitsunobu conditions [122].

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Published 29 Jun 2018

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SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

Anomeric modification of carbohydrates using the Mitsunobu reaction

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives