270075-72-4

Basic information

• Product Name: phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside
• Synonyms: phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside
• CAS NO: 270075-72-4
• Molecular Weight: 384.494
• Mol File: 270075-72-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside(270075-72-4)
• EPA Substance Registry System: phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside(270075-72-4)

Safety Data

• Hazardous Substances Data: 270075-72-4(Hazardous Substances Data)

Upstream product

• 4163-60-4 β-D-galactose peracetate 
• 144830-21-7 phenyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 231623-55-5 phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 138922-03-9 phenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 108-98-5 thiophenol 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 911684-18-9 phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 1176030-73-1 phenyl 1-thio-2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 1169758-41-1 phenyl 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-2-O-(2-naphthyl)methyl-1-thio-β-D-galactopyranoside 
• 124477-12-9 2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol 
• 124477-05-0 2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone 
• 124477-06-1 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone 
• 124477-03-8 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone 
• 124477-00-5 phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside 
• 124476-96-6 phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 124476-99-9 phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 124477-04-9 3,4-O-isopropylidene-2,6-di-O-methyl-β-D-galactopyranosyl phenyl sulphone 
• 124476-98-8 phenyl 3,4-O-isopropylidene-2,6-di-O-methyl-1-thio-β-D-galactopyranoside 
• 124477-11-8 1,5-anhydro-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-D-lyxo-hex-1-enitol 
• 270075-75-7 phenyl 2-O-benzyl-3,4,6-tri-O-lauroyl-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach

To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-l-rhamnopyranosyl-(1→2)-α-d-galactopyranosyl-(1→3)-α-l-rham

Mechanistic studies and methods to prevent aglycon transfer of thioglycosides

Thioglycosides have been employed extensively for the synthesis of complex oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful, aglycon transfer is a problematic side reaction with thioglycosides. In this paper, a series of mechanistic studies are described. The aglycon transfer process is shown to affect both armed and disarmed thioglycosides, cause anomerization of the carbon-sulfur bond of a thioglycoside, and destroy the product of a glycosylation reaction. The results indicate that the aglycon transfer process can be a major problem for a wide range of thioglycosides. This side reaction is especially important to consider when carrying out complex reactions such as solid-phase glycosylations, one-pot or orthogonal multicomponent glycosylations, and construction of carbohydrate libraries. To prevent transfer, a number of modified aglycons were examined. The 2,6-dimethylphenyl (DMP) aglycon was found to effectively block transfer in a variety of model studies and glycosylation reactions. The DMP group can be installed in one step from a commercially available thiol (2,6- dimethylthiophenol) and is useable as a glycosyl donor. On the basis of these features, the DMP group is proposed as a convenient and improved aglycon for thioglycosides.

A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide

The use of lipophilic, acyl-type protecting groups in the synthesis of higher-membered oligosaccharides is described by the example of oligosaccharides corresponding to the O-specific polysaccharide (O-SP) of Shigella dysenteriae type 1. Thus, O-stearoyla