Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-d-galactose

Schmölzer, Christoph; Nowikow, Christina; Kählig, Hanspeter; Schmid, Walther

doi:10.1016/j.carres.2012.11.019

Cited by 13 publications

(6 citation statements)

References 44 publications

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“…Allyl 3-O-Acetyl-2,6-dideoxy-2-trifluoroacetamido-β-D-glucopyranoside (29). Route a: A solution of diol 28 (11.5 g, 38.4 mmol, 1.0 equiv) in anhyd.…”

Section: Allyl 34-di-o-acetyl-2-deoxy-6-o-toluenesulfonyl-2-trifluoro...mentioning

confidence: 99%

“…Going beyond the original paths to 2-acetamido ,− and 2,4-diacetamido glycosides, − or post-glycosylation functionalization routes, − a large variety of advanced AAT intermediates featuring 2,4-orthogonal protecting groups were designed (Figure ). Most focus was on precursors to α-linked AAT for use in the synthesis of PS A1, − Sp1, ,,,− and Sp LTA. , Except for a precursor bearing a 2-imino group and stereotunable 2- N ,3- O -oxazolidinone donors, , intermediates set up for use as glycosylating agents basically feature a 2-azido moiety .…”

Section: Introductionmentioning

confidence: 99%

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Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine

2023

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We report the syntheses of 1,3,4-tri-O-acetyl-2-amino-2,6-dideoxy-β-d-glucopyranose and allyl 2-amino-2,6-dideoxy-β-d-glucopyranoside from d-glucosamine hydrochloride. The potential of these two versatile scaffolds as key intermediates to a diversity of orthogonally protected rare deoxyamino hexopyranosides is exemplified in the context of fucosamine, quinovosamine, and bacillosamine. The critical C-6 deoxygenation step to 2,6-dideoxy aminosugars is performed at an early stage on a precursor featuring an imine moiety or a trifluoroacetamide moiety in place of the 2-amino group, respectively. Robustness and scalability are demonstrated for a combination of protecting groups and incremental chemical modifications that sheds light on the promise of the yet unreported allyl 2,6-dideoxy-2-N-trifluoroacetyl-β-d-glucopyranoside when addressing the feasibility of synthetic zwitterionic oligosaccharides. In particular, allyl 3-O-acetyl-4-azido-2,4,6-trideoxy-2-trifluoroacetamido-β-d-galactopyranoside, an advanced 2-acetamido-4-amino-2,4,6-trideoxy-d-galactopyranose building block, was achieved on the 30 g scale from 1,3,4,6-tetra-O-acetyl-β-d-glucosamine hydrochloride in 50% yield and nine steps, albeit only two chromatography purifications.

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“…Allyl 3-O-Acetyl-2,6-dideoxy-2-trifluoroacetamido-β-D-glucopyranoside (29). Route a: A solution of diol 28 (11.5 g, 38.4 mmol, 1.0 equiv) in anhyd.…”

Section: Allyl 34-di-o-acetyl-2-deoxy-6-o-toluenesulfonyl-2-trifluoro...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine

2023

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“…In addition, many other diverse reduction processes have been effected by the H-Cube ® system. It has been utilised for the reduction of amides [239], nitro compounds [240][241][242], nitriles [243][244][245], azides [246,247], diazo compounds [248], and for carrying out reductive aminations [249][250][251] on a laboratory scale, while the H-Cube ® midi, has been designed specifically to be used in larger scale processes [252][253][254]. Recently, the H-Cube ® apparatus has also found use in the evaluation for biomass-derived chemicals recovery, such as Ru-catalysed hydrogenation of methyl levulinate (262) from lignocellulosic biomass to γ-valerolactone (263) [255], and scrap waste recovery, such as the scrap ceramic-cores of automotive catalytic converters (CATs) employed in the chemoselective hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol [256,257].…”

Section: Hydrogenationmentioning

confidence: 99%

“…The CSM designs enhance the biphasic mixing ensuring a high interfacial contact area. Such Scheme 58: Continuous hydrogenation system for the preparation of cyrene ( 241) from (−)-levoglucosenone (240).…”

Section: Hydrogenationmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…35 RANEY® nickel catalysis effects the aliphatic nitro reduction of 3 at relatively mild conditions affording amine 4 in near quantitative yields (Scheme 1). 37 Given the high yields of the aforementioned protocols they are ideally suited for incorporation into sequential cascade reaction sequences. As an example, utilising the H-cube, the reduction of 5 and subsequent cyclisation using flow hydrogenation was reported to afford indole 6 in near quantitative yield (Scheme 2).…”

Section: Nitro Reductionsmentioning

confidence: 99%

The expanding utility of continuous flow hydrogenation

et al. 2015

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There has been an increasing body of evidence that flow hydrogenation enhances reduction outcomes across a wide range of synthetic transformations. Moreover flow reactors enhance laboratory safety with pyrophoric catalysts contained in sealed cartridges and hydrogen generated in situ from water. This mini-review focuses on recent applications of flow chemistry to mediate nitro, imine, nitrile, amide, azide, and azo reductions. Methodologies to effect de-aromatisation, hydrodehalogenation, in addition to olefin, alkyne, carbonyl, and benzyl reductions are also examined. Further, protocols to effect chemoselective reductions and enantioselective reductions are highlighted. Together these applications demonstrate the numerous advantages of performing hydrogenation under flow conditions which include enhanced reaction throughput, yields, simplified workup, and the potential applicability to multistep and cascade synthetic protocols.

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Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-d-galactose

Cited by 13 publications

References 44 publications

Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine

Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

The expanding utility of continuous flow hydrogenation

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