74352-41-3

Basic information

• Product Name: 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• Synonyms: 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• CAS NO: 74352-41-3
• Molecular Weight: 633.808
• Mol File: 74352-41-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(74352-41-3)
• EPA Substance Registry System: 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(74352-41-3)

Safety Data

• Hazardous Substances Data: 74352-41-3(Hazardous Substances Data)

Upstream product

• 2127-03-9 2,2'-dipyridyldisulphide 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 2637-34-5 2-Sulfanylpyridine 
• 2297-41-8 pyridin-2-yl 1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 141739-72-2 2-mercaptopyridine methanesulfonate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 74352-37-7 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(pyridin-2-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 82300-67-2 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 93414-74-5 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 96689-95-1 (2R,3R,4R,5S,6R)-2-(2,4-Dimethoxy-phenyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 73244-62-9 (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol 
• 124917-60-8 tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose 
• 73244-61-8 α-1-deoxy-1-(2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 149933-24-4 Methyl 2,3-di-O-benzyl-6-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-xylo-hex-5-enopyranoside 
• 85422-91-9 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 86762-94-9 2,4,6-Trimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 
• 96689-96-2 α-1-deoxy-1-(C-2',4'-dimethoxyphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 89648-16-8 β-D-glucopyranosyl-2,4,6-trimethoxybenzene 
• 96689-92-8 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 

Relevant articles and documents

Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy

While strategies involving a 2e- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demonstrated by the mild reaction conditions enabling the synthesis of challenging α-1,2-cis-thioglycosides, the tolerance of various functional groups and the broad substrate scope for both common pentoses and hexoses. Furthermore, this general approach is compatible with both sp2 and sp3 sulfur electrophiles and late-stage glycodiversification for a total of 50 substrates probed.

Synthesis and Reductive Elimination Reactions of Aryl Thioglycosides

Treatment of the sugar hemiacetals 1, 5, 7, 10, 12 and 14 with ArSSAr (Ar = phenyl, 2-pyridyl, 2-benzothiazolyl) and trialkylphosphanes affords in an SN2 process the corresponding aryl thioglycosides 3, 6, 8, 9, 11, 13, 15 and 16 in good to exc

C-GLYCOSIDATION OF PYRIDYL THIOGLYCOSIDES

The pyridylthioglycosides 1 are efficiently transformed into the corresponding C-glycosides via reaction with silver(I) triflate and a variety of carbon nucleophiles.