20113-43-3

Upstream product

• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 50-99-7 D-glucose 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-24-7 acetic anhydride 
• 6619-07-4 6-O-toluolsulfonyl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 67-66-3 chloroform 
• 7646-78-8 tin(IV) chloride 
• 7601-90-3 perchloric acid 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 

Downstream Products

• 24871-54-3 acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside 
• 69240-09-1 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol 
• 871011-08-4 2,3,4-tri-O-acetyl-1-S-methylsulfonyl-6-O-(4-methylphenylsulfonyl)-1-thio-β-D-glucose 
• 871010-58-1 2,3,4-tri-O-acetyl-6-S-acetyl-S-phenylsulfonyl-1,6-dithio-β-D-glucose 
• 59202-80-1 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors

New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.

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.

The synthesis of various 1,6-disulfide-B ridged D-hexopyranoses

1,6-Disulfide-bridged derivatives have been prepared for D-gluco-, D-manno-, D-allo-, D-galacto-, and D-talopyranose, in the main by the nucleophilic attack of a C6 thiolate onto an anomeric thiosulfonate. The D-gluco disulfide, 'angyalosan', was successfully oxidized to a single thiosulfinate. CSIRO 2005.

Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y

Sulfur-linked analogues of 3-O-α-D-glucopyranosyl-D-glucose (nigerose), 3-O-β-D-glucopyranosyl-D-glucose (laminarabiose), 6-O-β-D-glucopyranosyl-D-glucose (gentiobiose), O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranosyl-(1 → 3)-D-glucose (laminaratriose), O-β-D-glucopyranosyl-(1 → 6)-O-β-D-glucopyranosyl-(1 → 6)-D-glucose (gentiotriose) and 3,6-di-O-β-D-glucopyranosyl-D-glucose (laminaran trisaccharide Y), namely, respectively, 3-thionigerose (6), 3-thiolaminarabiose (II), 6-thiogentiobiose (21), 3(I),3(II)-dithiolaminaratriose (16), 6(I),6(ii)-dithiogentiotriose (29) and 3(I),6(I)-dithiolaminaran trisaccharide Y (37) have been conveniently prepared by S(N)2 reactions of the corresponding anomer of D-glucopyranose 1-thiolate with suitably activated monosaccharide derivatives in N,N-dimethylformamide (for 6 and 21) or in tetrahydrofuran in the presence of a crown ether (for 11). A sequence involving the reaction of non-anomeric thiolates with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was alternatively used for the preparation of 11 and 21 but proved less satisfactory. The preparation of thiotrisaccharides 16, 29, and 37 involved a mixed approach.

Use of Ferric Chloride in Carbohydrate Reactions: Part V - Acetolysis of Methyl Hexopyranosides Using Ferric Chloride in Acetic Anhydride

Treatment of methyl α-D-gluco- and galacto-pyranosides with acetic anhydride-ferric chloride reagent results in the acetolysis of the glycosides.Anomeric mixtures of the sugar peracetates in their pyranose and furanose forms and acyclic peracetates are obtained.The rate of acetolysis is retarded by the introduction of a tosyl function at position-6.