3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry

Andersen, Sofie Meng; Heuckendorff, Mads; Jensen, Henrik H.

doi:10.1021/acs.orglett.5b00041

Cited by 44 publications

(51 citation statements)

References 26 publications

(32 reference statements)

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“…Known reducing sugars bearing acetyl (12), [31] benzoyl (13), [32,33] and benzyl (15,16) [34] protecting groups were acylated -selectively as described above to give donors 17, 18, 20, and 21, respectively. Known reducing sugars bearing acetyl (12), [31] benzoyl (13), [32,33] and benzyl (15,16) [34] protecting groups were acylated -selectively as described above to give donors 17, 18, 20, and 21, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Glycosyl ortho‐Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

et al. 2016

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We describe the β‐ortho‐methoxybenzoate as a shelf stable and practical C‐1 nucleofuge for catalytic chemical glycosylation in which the benzoic acid by‐product can be easily removed, reisolated, and potentially recycled after the glycosylation reaction. This new type of glycosyl donor can be efficiently activated by a range of promoters, including Bi(OTf)3, Fe(OTf)3, TMSOTf (TMS = trimethylsilyl), and triflic acid, with low (<10 mol‐%) catalyst loadings. The donor shows higher reactivity than analogous benzoate, p‐methoxybenzoate and p‐cyano‐o‐methoxybenzoate donors. In glycosylation reactions with o‐methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate‐based secondary alcohol. Furthermore, β‐selective mannosylation was achieved with a Crich‐type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first step of a one‐pot two‐step glycosylation to obtain a trisaccharide; the second coupling involved activation of a thioglycoside with NIS/TMSOTf (NIS = N‐iodosuccinimide). We believe that this offers a good alternative to current protocols.

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Section: Resultsmentioning

confidence: 99%

“…Tetra-O-acetyl-1-O-(o-methoxybenzoyl)--D-glucopyranose (17): Glucose lactol 12[31] (2.00 g, 5.74 mmol, 1.0 equiv. ), omethoxybenzoyl chloride (2; 2.45 g, 14.4 mmol, 2.5 equiv.…”

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confidence: 99%

Glycosyl ortho‐Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

et al. 2016

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“…This reaction required some optimization. Three different benzoylated mannosyl donors were used for this purpose: the trichloroacetimidate 5 , the N ‐phenyl trifluoroacetimidate 6 , and the 5‐ tert ‐butyl‐2‐methylphenylsulfanyl derivative 7 . We selected benzoyl protecting groups instead of acetate moieties in order to prevent undesired side reactions such as the formation of glycosyl orthoesters or acid‐mediated acetyl transfer …”

Section: Resultsmentioning

confidence: 99%

A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion

et al. 2019

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We have recently demonstrated, by employing azobenzene glycosides, that bacterial adhesion to surfaces can be switched through reversible reorientation of the carbohydrate ligands. To investigate this phenomenon further, we have turned here to more complex—that is, multivalent—azobenzene glycoclusters. We report on the synthesis of a photosensitive trivalent cluster mannoside conjugated to an azobenzene hinge at the focal point. Molecular dynamics studies suggested that this cluster mannoside, despite the conformational flexibility of the azobenzene‐glycocluster linkage, offers the potential for reversibly changing the glycocluster's orientation on a surface. Next, the photoswitchable glycocluster was attached to human cells, and adhesion assays with type 1 fimbriated Escherichia coli bacteria were performed. They showed marked differences in bacterial adhesion, dependent on the light‐induced reorientation of the glycocluster moiety. These results further underline the importance of orientational effects in carbohydrate recognition and likewise the value of photoswitchable glycoconjugates for their study.

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“…Following peracetylation, selective removal of the anomeric acetate was accomplished using 3-(dimethylamino)-1-propylamine (DMAPA). 38 Finally, the anomeric hemiacetal was converted to its triisopropyl silyl ether using standard Corey conditions (imidazole and DMF) 39 to provide b-silyl ether 6 as a single anomer in 54% yield for the 4-step sequence. We initially attempted to advance substrate 6 to its triol 7 using sodium methoxide in methanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of lacto- N -tetraose

Craft

Townsend

2017

Carbohydrate Research

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Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue in glycobiology due to the challenge of isolating appreciable quantities of homogenous HMOs from breast milk. Herein, we report the synthesis of the human milk tetrasaccharide lacto-N-tetraose (LNT). LNT is ubiquitous in human breast milk as it is a core structure common to longer-chain HMOs and many glycolipids.

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3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry

Cited by 44 publications

References 26 publications

Glycosyl ortho‐Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

Glycosyl ortho‐Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion

Synthesis of lacto- N -tetraose

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