28244-97-5

Basic information

• Product Name: phenyl-1-thio-α-D-galactopyranoside
• Synonyms: phenyl-1-thio-α-D-galactopyranoside
• CAS NO: 28244-97-5
• Molecular Weight: 272.322
• Mol File: 28244-97-5.mol
• Article Data: 97

Chemical Properties

• CAS DataBase Reference: phenyl-1-thio-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl-1-thio-α-D-galactopyranoside(28244-97-5)
• EPA Substance Registry System: phenyl-1-thio-α-D-galactopyranoside(28244-97-5)

Safety Data

• Hazardous Substances Data: 28244-97-5(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 75-77-4 chloro-trimethyl-silane 
• 4551-15-9 phenylthiotrimethylsilane 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 530-26-7 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 7322-31-8 β-D-mannose 
• 7296-15-3 alpha-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 17314-33-9 tributyltin phenyl sulfide 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 262605-68-5 phenyl 6-O-triphenylmethyl-1-thio-α-D-mannopyranoside 
• 263543-42-6 phenyl 3,4-O-(2’,3’-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside 
• 310870-40-7 phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 488714-68-7 phenyl 2,6-di-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 
• 488714-69-8 phenyl 3,6-di-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 
• 225241-34-9 phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 252209-20-4 phenyl 4,6-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 236115-71-2 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside 
• 213998-04-0 phenyl 3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 71676-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 210295-04-8 phenyl 3,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 
• 197631-83-7 phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 152488-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2- Cis-Selective Glucosylation of Reactive Alcohols

Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2-cis-selectivity when activated with TMS-I in the presence of triphenylphosphine oxide. Stereoselectivity is dependent on the number of trifluoromethyl groups (4-trifluoromethylbenzyl vs 3,5-bis-trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2-cis-selectivity with reactive alcohol acceptors.