Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

Osman, Hasnah; Larsen, David S.

doi:10.1016/j.tet.2009.03.092

Cited by 7 publications

(3 citation statements)

References 33 publications

(35 reference statements)

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“…The chloracetyl group can be readily removed with thiourea as an acceptor for glycosylation 7c. Thioglycoside 33 was converted into the corresponding glycosyl bromide 3 with IBr in 72 % yield 20. In addition, regioselective benzylation of the C‐3 hydroxy of 30 by treatment with dibutyltin oxide, followed by reaction with benzyl bromide in the presence of CsF in DMF afforded 34 in 63 % yield.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux

Cao

et al. 2014

ChemMedChem

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The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux

Cao

et al. 2014

ChemMedChem

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“…In our initial experiments, we have chosen l -rhamnal as a sugar substituent, due to its commercial availability and easy transformation into derivatives of deoxypyranosides—the structural analogs of well-known antibiotic sugars [34,35,36].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

et al. 2014

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A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15-17 were synthesized by treating ω-bromoalkyl C-glycosides derived from L-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.

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“…Lewis-acid-promoted O - → C -glycoside rearrangements involving the initial formation of O -glycoside intermediates ( A ) followed by Fries-like O → C rearrangements were utilized effectively for the synthesis of C -aryl glycosides (Scheme ). − ,,,− As an example, Sc(OTf) 3 -promoted glycosylation of 2-deoxyglycosyl acetates with substituted phenols provided complex β- C -aryl glycosides 405 – 407 in excellent yields. ,, Upon use of SnCl 4 as the activator, complex C -aryl glycosides 408 and 409 were obtained in good yields as the β-anomers. , Under the conditions of Cp 2 HfCl 2 /AgClO 4 , similar reactions led to β- C -aryl glycosides 410 and 411 as single regio- and diastereoisomers in moderate yields. , Additionally, the glycosylation of glycosyl acetate with naphthol in the presence of BF 3 ·OEt 2 proceeded smoothly to give β- C -aryl glycosides 412 in 73% yield …”

Section: C-glycosylation With Glycosyl Acetatesmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of C-Glycosides

2017

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Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.

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Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

Cited by 7 publications

References 33 publications

Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux

Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux

Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

Recent Advances in the Chemical Synthesis of C-Glycosides

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