23643-29-0

Usage

Uses

Used in Pharmaceutical Industry:
1,6-ANHYDRO is used as an intermediate in the synthesis of complex carbohydrate structures for pharmaceutical applications. Its unique chemical properties allow for the creation of novel drug candidates with potential therapeutic benefits.
Used in Chemical Synthesis:
1,6-ANHYDRO is used as a key building block in the synthesis of various anhydro sugars, which are important components in the development of new chemical compounds and materials. Its versatility in chemical reactions makes it a valuable asset in the field of organic chemistry.
Used in Research and Development:
1,6-ANHYDRO is utilized as a research tool in the study of carbohydrate chemistry and its role in biological systems. Its unique structure provides insights into the mechanisms of carbohydrate interactions and can lead to the discovery of new biological processes and potential therapeutic targets.
Used in Material Science:
1,6-ANHYDRO is employed in the development of advanced materials, such as polymers and coatings, that leverage the unique properties of anhydro sugars. Its incorporation into these materials can result in improved performance characteristics, such as enhanced stability and resistance to degradation.

InChI:InChI=1/C13H16O7S/c1-7-2-4-8(5-3-7)21(16,17)20-12-9-6-18-13(19-9)11(15)10(12)14/h2-5,9-15H,6H2,1H3/t9-,10-,11-,12-,13-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 498-07-7 levoglucosan 

Downstream Products

• 33557-13-0 1,6-anhydro-4-deoxy-4-fluoro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 29332-85-2 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside 
• 1450824-22-2 (2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-sulfanylbis(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol) 
• 27108-04-9 4-deoxy-4-fluoro-β-D-glucopyranose 
• 62182-11-0 3-fluoro-3-deoxy-α-D-glucose 
• 33208-46-7 1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose 

Relevant academic research and scientific papers

Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade: Payne rearrangement/azidation process leading to 3-azido-galactopyranose. The latter intermediate was efficiently converted into TD139 in a few simple and practical steps.

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.

Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose

There is a growing interest in the preparation of polyfluorinated carbohydrates. A limited number of fluorohexopyranosides have been used in biological investigations because of the synthetic challenge they present. Hence, we report the synthesis of fluor

1H NMR STUDY OF 1,6-ANHYDRO-β-D-GLUCOPYRANOSE TOSYLATED AT 2- AND/OR 4-POSITION

The 1H nmr spectra of 1,6-anhydro-2-O-tosyl-, 1,6-anhydro-4-O-tosyl and 1,6-anhydro-2,4-di-O-tosyl-β-D-glucopyranose have been analyzed.The data allow to discriminate between the two monosubstituted levoglucosans.