3971-48-0

Usage

Chemical compound

1,5-anhydro-D-galactitol is a chemical compound that is a derivative of galactose.

Sugar alcohol

It is a sugar alcohol that is found in small amounts in some natural sources, such as certain fruits and vegetables.

Therapeutic effects

1,5-anhydro-D-galactitol has been studied for its potential therapeutic effects in the treatment of certain medical conditions, such as diabetes and inflammation.

Role in disease

It has been investigated for its role in the development and progression of certain diseases, including cancer.

Ongoing research

Research on 1,5-anhydro-D-galactitol is ongoing, and further studies are needed to fully understand its potential benefits and risks for human health.

Upstream product

• 59-23-4 D-Galactose 
• 19200-39-6 N,N-diethyl β-D-galactopyranosyl dithiocarbamate 
• 55529-70-9 per-O-trimethylsilyl-D-galactopyranoside 
• 7464-38-2 2-naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4133-45-3 methyl 2,3,4,6-tetra-O-trimethylsilyl-α-D-galactopyranoside 
• 2296-39-1 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-β-D-galactopyranoside 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 162060-53-9 1,5-anhydro-3,4,6-tri-O-benzyl-D-galactitol 
• 82682-67-5 (2R,3S,4R,5S)-3,4,5-Tris-trimethylsilanyloxy-2-trimethylsilanyloxymethyl-tetrahydro-pyran 
• 13121-62-5 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-galactitol 

Downstream Products

• 85906-19-0 1,5-anhydro-2,3,4-tri-O-benzoyl-6-O-p-tolylsulfonyl-D-galactitol 
• 109010-33-5 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 1204228-81-8 1,5-anhydro-4,6-O-benzylidene-D-galactitol 
• 88043-87-2 1,5-anhydro-4,6-di-O-benzoyl-D-galactitol 
• 74629-56-4 1,5-anhydro-3,4,6-tri-O-benzoyl-D-galactitol 
• 65371-05-3 1,5-anhydro-3,6-di-O-p-tolylsulfonyl-D-galactitol 
• 65371-03-1 1,5-anhydro-2,3,6-tri-O-p-tolylsulfonyl-D-galactitol 
• 65371-00-8 1,5-anhydro-2,3,4,6-tetra-O-p-tolylsulfonyl-D-galactitol 
• 85906-16-7 1,5-anhydro-6-O-p-tolylsulfonyl-D-galactitol 
• 143916-17-0 1,5-anhydro-3,4-O-isopropylidene-6-O-trityl-D-galactitol 
• 143916-18-1 2-O-acetyl-1,5-anhydro-3,4-O-isopropylidene-6-O-trityl-D-galactitol 
• 1170714-29-0 1,5-anhydro-6-O-tert-butyldiphenylsilyl-D-galactitol 
• 126923-31-7 C₁₃H₁₆O₅ 

Relevant academic research and scientific papers

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst

The feedstocks from biomass are defined and limited by nature, but through the choice of catalyst, one may change the deoxygenation outcome. We report divergent but selective deoxygenation of sugars with triethylsilane (TESH) and two fluoroarylborane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3). To illustrate, persilylated 2-deoxyglucose shows exocyclic C-O bond cleavage/reduction with the less sterically congested BAr3,5-CF3, whereas endocyclic C-O bond cleavage/reduction predominates with the more Lewis acidic B(C6F5)3. Chiral furans and linear polyols can be selectively synthesized depending on the catalysts. Mechanistic studies demonstrate that the resting states of these catalysts are different.

First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

An efficient method for the preparation of 1,5-anhydroalditol from unprotected carbohydrates via glycopyranosyl iodide

A practical, facile method was developed for the preparation of 1,5-anhydroalditol via per-O-TMS-glycopyranosyl iodide with LiBH4. A series of 1,5-anhydroalditols were prepared in excellent yields (up to 92%) from unprotected carbohydrates within 2 days under mild conditions. In addition, multi-gram scale preparation of 1,5-anhydroglucitol (1,5-AG), a major polyol present in human serum, was developed using the same procedure without the need for chromatographic purification.

Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics

Glycosyl amino acid mimetics of the typical GalNAc-(1→O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics.

Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.

Thermodynamics of binding of D-galactose and deoxy derivatives thereof to the L-arabinose-binding protein

We report the thermodynamics of binding of D-galactose and deoxy derivatives thereof to the arabinose binding protein (ABP). The "intrinsic" (solute-solute) free energy of binding ΔG°int at 308 K for the 1-, 2-, 3-, and 6-hydroxyl groups of gal

Original synthesis of linear, branched and cyclic oligoglycerol standards

A variety of authentic standards of linear, branched and cyclic oligomers of glycerol, with well-defined structures and degrees of polymerisation from 2 to 5, have been efficiently synthesised. Linear oligomers were obtained by means of a convergent approach based on regioselective opening of bis(epoxides) with solketal; branched compounds were synthesised using oxidative cleavage of the corresponding anhydrohexitols as the key step. A 6-exo-trig halocyclisation reaction involving heteroatom-tethered unsaturated alcohols permitted an efficient synthesis of the precursors of selected cyclic dimers; larger cyclic oligomers were prepared by two one-pot Williamson reactions using a ditriflate derived from diglycerol. All these methodologies permitted further scaling up.