495387-54-7

Usage

Type

Thiol derivative of D-xylitol (a sugar alcohol)

Structure

Contains a 1,4-anhydro ring, three benzyl groups (C6H5CH2-) at the 2nd, 3rd, and 5th positions, and a sulfur atom replacing the hydroxyl group at the 4th position

Synthesis

Multi-step process involving protection and deprotection of hydroxyl groups of xylitol

Appearance

White crystalline solid

Applications

Organic synthesis, building block for complex molecules, intermediate in the synthesis of pharmaceuticals and biologically active compounds

Reactivity

Unique structure and reactivity due to the presence of the sulfur atom and benzyl groups

Stability

Stable under normal conditions, but may be sensitive to oxidation or hydrolysis

Solubility

Likely soluble in organic solvents such as dichloromethane, ethyl acetate, or acetone, due to the presence of the benzyl groups

Purity

Typically characterized by techniques such as NMR, HPLC, or mass spectrometry to confirm the structure and purity of the compound

Safety

Handle with care, using appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat, as it may be harmful if inhaled, ingested, or comes into contact with the skin

Hazards

Potential hazards may include flammability, irritancy, or toxicity, depending on the specific reaction conditions and the presence of other chemicals

Disposal

Dispose of in accordance with local regulations and guidelines for chemical waste, preferably through a licensed waste disposal facility or by following proper chemical disposal procedures

Upstream product

• 532-20-7 L-arabinose 
• 96192-07-3 2,3,5-tri-O-benzyl-L-arabinofuranose 
• 131615-65-1 methyl 2,3,5-tri-O-benzyl-α,β-L-arabinofuranoside 
• 13039-64-0 (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol 
• 495387-53-6 2,3,5-tri-O-benzyl-1,4-di-O-methanesulfonyl-L-arabinitol 

Downstream Products

• 495387-55-8 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[[(2'S,3'S)-2',4'-O-benzylidene-3'-(sulfooxy)butyl]-episulfoniumylidene]-D-xylitol 

Relevant academic research and scientific papers

Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides

Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.

Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-xylitol at the least-hindered carbon of 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate. The sulfonium ion 8 inhibited barley-α-amylase (AMY1) and porcine pancreatic-α-amylase (PPA), with Ki values of 109 ± 11 and 55 ± 5 μM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.