80483-16-5

Usage

Uses

Used in Medicinal Chemistry:
2,6-Anhydro-1,5-dideoxy-L-arabino-hexa-5-enitol is used as a potential pharmaceutical candidate for [application reason] due to its unique molecular structure and properties that may contribute to the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2,6-Anhydro-1,5-dideoxy-L-arabino-hexa-5-enitol is used as a key intermediate or building block for the synthesis of complex organic molecules, leveraging its specific chemical reactivity and structural features.
Used as a Starting Material:
2,6-Anhydro-1,5-dideoxy-L-arabino-hexa-5-enitol is utilized as a starting material for the production of other compounds, particularly in the synthesis of novel carbohydrate-based molecules with potential applications in various industries.
(Note: The specific application reasons for medicinal chemistry, organic synthesis, and as a starting material would need to be filled in based on further research and understanding of the compound's properties and reactivity.)

Upstream product

• 80483-13-2 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 
• 54621-94-2 3,4-di-O-acetyl-L-fucal 

Downstream Products

• 137035-65-5 1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol 
• 137035-64-4 1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol 
• 91861-12-0 Benzoic acid (2S,3S,4S)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester 
• 130061-11-9 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-lyxo-hex-1-enitol 
• 130061-16-4 dibenzoyl fucal 
• 157430-14-3 (2S,3S,6S)-6-(4-Methoxy-phenoxy)-2-methyl-3,6-dihydro-2H-pyran-3-ol 
• 122900-89-4 (2S,3S,4S,4aS,5R,10R,10aR)-5-(2,4-Dinitro-phenylamino)-3,4-dihydroxy-9-methoxy-2-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]chromene-10-carbaldehyde 
• 144071-50-1 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxyl-lyxo-hex-1-enitol 
• 56733-55-2 (+)-(2S,3R)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 

Relevant academic research and scientific papers

Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.

Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

Stereospecific C-Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

A stereospecific Mizoroki–Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α- or β-aryl-C-glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization of cross-coupling conditions, various prepared glycals (7 examples) and arenes (10 examples) were tested, leading stereospecifically to the corresponding aryl-C-glycosides with a carbonyl group at C3, thus opening up new horizons for the total synthesis of glycosylated natural products.

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides

A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.

Synthesis of a selective inhibitor of a fucose binding bacterial lectin from Burkholderia ambifaria

Burkholderia ambifaria is a bacterium member of the Burkholderia cepacia complex (BCC), a closely related group of Gram-negative bacteria responsible for "cepacia syndrome" in immunocompromised patients. B. ambifaria produces BambL, a fucose-binding lecti

Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation.

[formula: see text] The synthesis of an all-alpha L-oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

Rhodium(II) catalyzed asymmetric cyclopropanation of glycals with ethyl diazoacetate

Carbenoid species generated from ethyl diazoacetate and catalytic Rh2(OAc)4 react smoothly and with a high degree of stereoselectivity with glycals resulting in the predominant formation of doubly branched adducts containing an α-exo

Selective Deprotection of Esters Using Magnesium and Methanol

The use of magnesium metal in methanol for the deprotection of alkyl esters is described.This mild reagent also provides good to excellent selectivity to cleave different esters.The order of reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate > acetate > benzoate > pivaliate >> trifluoroacetamide.

Two pyran type glycosides from saponaria and dianthus

2,3-Dihydro 4-O-β-D-glucopyranosyl 3-hydroxy-2-methyl-4H-pyran was isolated from Saponaria officinallis and its relative configuration and conformation determined. A new glycoside, isomeric with the former but having a different configuration at C-4, has been isolated from Dianthus barbatus and D. deltoides.