3868-05-1

Usage

Uses

Used in Pharmaceutical Industry:
1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable building block for creating complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is used as a key reactant in the syntheses of anhydro sugars. These anhydro sugars are important in the development of novel compounds with specific properties, such as improved stability or reactivity, which can be applied in various chemical and industrial processes.
Used in Research and Development:
Due to its unique structure and properties, 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is also used in research and development for exploring new chemical reactions and understanding the behavior of similar compounds. This can lead to the discovery of new applications and advancements in various scientific fields.

Upstream product

• 492-61-5 β-D-glucose 
• 98-59-9 p-toluenesulfonyl chloride 
• 1071534-24-1 O¹,O³,O⁴-triacetyl-O²,O⁶-bis-(toluene-4-sulfonyl)-β-D-glucopyranose 
• 498-07-7 levoglucosan 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 16939-77-8 1,6:3,4-dianhydro-β-D-galactopyranose 

Downstream Products

• 88142-91-0 1,6-anhydro-2-O-p-toluenesulphonyl-3,4-O-bis(trimethylsilyl)-β-D-glucopyranose 
• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 
• 29332-85-2 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside 
• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 
• 4631-19-0 3,4,6-tri-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranosyl bromide 
• 4581-93-5 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranose 
• 4627-39-8 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-β-D-glucopyranose 

Relevant academic research and scientific papers

PROCESS FOR THE PRODUCTION OF 1,6-ANHYDRO SUGARS

Method for synthesizing 1,6-anhydro sugars – in particular sugars that may be used as intermediates for making fondaparinux.

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

Preparation method of fondaparinux sodium monosaccharide intermediate

The invention discloses a preparation method of a fondaparinux sodium monosaccharide intermediate. The preparation method comprises the following steps: (1) in the presence of an acid-binding agent, carrying out esterification reaction on a compound as shown in a formula (I) and a substituent sulfonic anhydride and/or a substituent sulfonyl halogen to generate a compound as shown in a formula (II); (2) carrying out a ring opening reaction on the compound as shown in the formula (II) in an acidic condition to generate a compound as shown in a formula (III); (3) carrying out benzylation reactionon the compound as shown in the formula (III) and benzyl monohalide in an alkaline condition to generate a compound as shown in a formula (IV); and (4) carrying out an azido reaction on the compoundas shown in the formula (IV) and alkali metal azide salt to generate a compound as shown in a formula (V) and caring out inner ether ring opening and acetylation reaction on the compound as shown in the formula (V) in a mixed solution of acetic anhydride and trifluoroacetic acid to generate a compound as shown in a formula (VI). The method can be used for obtaining an ideal product yield, and theraw materials are cheap, easily available and relatively few in three wastes. The formulae are as shown in the description.

PREPARATION OF 1,6:3,4-DIANHYDRO-β-D-ALTROPYRANOSE AS STARTING SUBSTANCE FOR THE SYNTHESIS OF 3-SUBSTITUTED D-MANNOSE DERIVATIVES

Acetolysis of 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-galactopyranose (I) gave 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose (II) which was converted with sodium methoxide to 1,6:3,4-dianhydro-β-D-altropyranose (X).The 1,6-anhydride bond in diacetate II was cleaved with acetic anhydride or hydrogen bromide in acetic acid under formation of a mixture of anomeric tetraacetates of 2-O-p-toluenesulfonyl-D-glucopyranose or the corresponding acetates of α-D-glucopyranosyl bromide XIII and its 6-bromo-6-deoxy derivative XIV.

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.