141193-62-6

Basic information

• Product Name: Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid
• Synonyms: Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid
• CAS NO: 141193-62-6
• Molecular Weight: 382.434
• Mol File: 141193-62-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid(141193-62-6)
• EPA Substance Registry System: Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid(141193-62-6)

Safety Data

• Hazardous Substances Data: 141193-62-6(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 26905-22-6 hydroxymethyl phenyl sulfide 
• 142757-88-8 2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranosyl trichloroacetimidate 
• 1251750-15-8 phenyl 2,3,4-tri-O-acetyl-6-phenoxythiocarbonyl-1-thio-β-D-galactopyranoside 
• 73-34-7 D-Fucose 
• 108-24-7 acetic anhydride 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 

Downstream Products

• 101696-00-8 phenyl 6-deoxy-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 141115-74-4 Benzyl-O-(2,3,4-tri-O-benzoyl-6-desoxy-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid 
• 141020-11-3 Benzyl-O-(2,3,4-tri-O-benzoyl-6-desoxy-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid 
• 141020-12-4 Benzyl-O-(2,3,4-tri-O-benzoyl-6-desoxy-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-desoxy-α-D-galactopyranosid 
• 141020-09-9 Phenyl-2,3,4-tri-O-benzoyl-6-desoxy-1-thio-β-D-galactopyranosid 
• 87321-98-0 Benzyl-O-(6-desoxy-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-desoxy-α-D-galactopyranosid 
• 257936-60-0 methyl O-(2,3-di-O-benzoyl-4-O-chloroacetyl-6-deoxy-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-68-8 methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-76-8 methyl O-(4-O-chloroacetyl-6-deoxy-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-78-0 methyl O-(6-deoxy-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-58-6 phenyl 2,3-di-O-benzoyl-4-O-chloroacetyl-6-deoxy-1-thio-β-D-galactopyranoside 
• 257936-74-6 phenyl 4-O-chloroacetyl-6-deoxy-2,3-di-O-pivaloyl-1-thio-β-D-galactopyranoside 
• 257936-53-1 phenyl 2,3-di-O-benzoyl-6-deoxy-1-thio-β-D-galactopyranoside 
• 257936-72-4 phenyl 6-deoxy-2,3-di-O-pivaloyl-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs

This work investigates the addition of monosaccharides to marketed drugs to improve their pharmacokinetic properties for oral absorption. To this end, a set of chloromethyl glycoside synthons were developed to prepare a variety of glycosyloxymethyl-prodrugs derived from 5-fluorouracil, thioguanine, propofol and losartan. Drug release was studied in vitro using β-glucosidase confirming rapid conversion of the monosaccharide prodrugs to release the parent drug, formaldehyde and the monosaccharide. To showcase this prodrug approach, a glucosyloxymethyl conjugate of the tetrazole-containing drug losartan was used for in vivo experiments and showed complete release of the drug in a dog-model.

The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding

α-Gal epitopes (also termed as α-Gal) are carbohydrate structures bearing the α-D-Gal-(1→3)-β-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of α-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized α-Gal derivatives. 4-Deoxy-α-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard α-Gal epitopes α-D-Gal-(1→3)-β-D-Gal-(1→4)-β-D-Glc-NHAc (39) and α-D-Gal-(1→3)-β-D-Gal-(1→4)-β-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-α-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-α-Gal derivative 8 exhibited similar antibody recognition to both α-Gal epitope 39 and α-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other α-Gal derivatives.