55500-08-8

Basic information

• Product Name: 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide
• Synonyms: 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide
• CAS NO: 55500-08-8
• Molecular Weight: 523.356
• Mol File: 55500-08-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide(55500-08-8)
• EPA Substance Registry System: 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide(55500-08-8)

Safety Data

• Hazardous Substances Data: 55500-08-8(Hazardous Substances Data)

Upstream product

• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 6619-07-4 6-O-p-toluenesulfonyl-D-mannopyranose 
• 530-26-7 D-Mannose 
• 78478-66-7 1,2,3,4-tetra-O-acetyl-6-O-deoxy-6-tosyl-α/β-D-mannopyranose 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 50-99-7 D-glucose 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 7446-70-0 aluminium trichloride 
• 67-66-3 chloroform 
• 95118-61-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose 

Downstream Products

• 121965-37-5 O¹-(4-acetoxy-3-methoxy-benzoyl)-O²,O³,O⁴-triacetyl-O⁶-(toluene-4-sulfonyl)-β-D-glucopyranose 
• 103725-98-0 2,3,4-tri-O-acetyl-6-O-tosyl-β-D-glucopyranose 1-(dibenzyl phosphate) 
• 106192-41-0 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranosyl azide 
• 312300-77-9 1,2-di-O-octadecyl-3-O-(2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-β-D-glucopyranosyl)glycerol 
• 1206797-11-6 C₂₀H₂₆O₁₁S 
• 1207854-30-5 C₂₁H₂₈O₁₁S 
• 1206797-14-9 C₂₂H₂₆O₁₁S 
• 1333231-24-5 (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-carboxymethyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose 
• 1333231-19-8 (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose 
• 1333231-22-3 (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-carboxylmethyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose 
• 1333231-18-7 (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose 
• 1333231-21-2 (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-carboxymethyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose 
• 1333231-17-6 (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose 
• 1333231-14-3 allyl 3,4-di-O-benzoyl-6-azido-α-D-mannopyranoside 

Relevant articles and documents

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1,6-Anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan) and the corresponding sulfoxides and sulfone

Starting 1,2,3,4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by 1H and 13C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.

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The β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.The key intermediate 14, which was uti