220645-20-5

Basic information

• Product Name: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside
• Synonyms: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside
• CAS NO: 220645-20-5
• Molecular Weight: 586.875
• Mol File: 220645-20-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside(220645-20-5)
• EPA Substance Registry System: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside(220645-20-5)

Safety Data

• Hazardous Substances Data: 220645-20-5(Hazardous Substances Data)

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-24-7 acetic anhydride 
• 106-45-6 para-thiocresol 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 136945-13-6 [(2R,3S,4R,5R)-3,4-diacetoxy-6-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl acetate 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 90-76-6 2-deoxy-2-amino glucose 
• 323195-39-7 p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 

Downstream Products

• 1616703-76-4 28-O-benzyl-3-O-[3′,4′,6′-tri-O-acetyl-2′-deoxy-2′-(2″,2″,2″-trichloroethyloxycarbonylamino)-β-D-glucopyranosyl]oleanolic ester 
• 1407151-68-1 C₃₀H₂₈Cl₃NO₇S 
• 1407151-96-5 p-tolyl 6-O-[3,4,6-tri-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-β-D-glucopyranosyl]-3-O-benzoyl-4-O-benzyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxythio-β-D-glucopyranoside 
• 1407151-95-4 p-tolyl 6-O-[3,4,6-tri-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-β-D-glucopyranosyl]-2,3,4-tri-O-benzylthio-β-D-glucopyranoside 
• 1407151-69-2 p-tolyl 2-O-benzoyl-2-O-benzyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxythio-β-D-glucopyranoside 
• 1309834-96-5 C₂₇H₂₇N₃O₅S 
• 501088-52-4 C₂₇H₂₅N₃O₅S 
• 501088-45-5 p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-thio-β-D-glucopyranoside 
• 133940-44-0 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 

Relevant articles and documents

Design, synthesis and cytotoxic activity of N-Modified oleanolic saponins bearing A glucosamine

A series of N-acyl, N-alkoxycarbonyl, and N-alkylcarbamoyl derivatives of 2′-deoxy-glucosyl bearing oleanolic saponins were synthesized and evaluated against HL-60, PC-3, and HT29 tumor cancer cells. The SAR studies revealed that the activity increased in order of conjugation of 2′ -amino group with carbamate > amide > urea derivatives. Lengthening the alkyl chain increased the cytotoxicity, the peak activity was found to around heptyl to nonyl substitutions. 2′-N-heptoxycarbonyl derivative 56 was found to be the most cytotoxic (IC50 = 0.76 μM) against HL-60 cells. Due to the interesting SARs of alkyl substitutions, we hypothesized that their location in the cell was different, and pursued a location study using 2′-(4″-pentynoylamino) 2′-deoxy-glucosyl OA, which suggested that these compounds distributed mainly in the cytosol.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides

Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for d-galactose and l-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated.