20113-43-3

Basic information

• Product Name: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose
• Synonyms: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose
• CAS NO: 20113-43-3
• Molecular Weight: 502.496
• Mol File: 20113-43-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose(20113-43-3)
• EPA Substance Registry System: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose(20113-43-3)

Safety Data

• Hazardous Substances Data: 20113-43-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 6619-07-4 6-O-toluolsulfonyl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 98-59-9 p-toluenesulfonyl chloride 
• 50-99-7 D-glucose 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 67-66-3 chloroform 
• 7646-78-8 tin(IV) chloride 
• 7601-90-3 perchloric acid 
• 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 
• 59202-80-1 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 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 

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.

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.