174356-26-4

Basic information

• Product Name: 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-D-
• Synonyms: 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-D-;1,3,4,6-Tetra-O-acetyl-2-deoxy-2-(tetrachlorophthalamido)-D-glucopyranose;1,3,4,6-Tetra-O-acetyl-2-deoxy-2-(tetrachlorophthalamido)-D-glucopyranose ,98%;2-Deoxy-2-(tetrachlorophthaliMido)-D-glucopyranose1,3,4,6-tetraacetate(MixofαandβanoMers)
• CAS NO: 174356-26-4
• Molecular Formula: C₂₂H₁₉Cl₄NO₁₁
• Molecular Weight: 615.2
• Mol File: 174356-26-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 676.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.62±0.1 g/cm3(Predicted)
• PKA: -4.28±0.20(Predicted)
• CAS DataBase Reference: 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-D-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-D-(174356-26-4)
• EPA Substance Registry System: 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-D-(174356-26-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 174356-26-4(Hazardous Substances Data)

Usage

Uses

1,3,4,6-Tetra-O-acetyl-2-tetrachlorophthalimide-2-deoxy-D-glucopyranose is an intermediate formed in the synthesis of N-Acetylchitooctaose (A168460), a chitooligosaccharide used to activate Saccharomyces cerevisiae chitin biosynthesis. N-Acetylchitooctaose has affinity for NKR-P1A protein, the major activating receptor at the surface of rat natural killer (NK) cells, and may be useful in human therapy in cancer treatment (colon cancer, melanoma).

Upstream product

• 117-08-8 tetrachlorophthalic anhydride 
• 108-24-7 acetic anhydride 
• 14131-62-5 D-glucosamine hydrochloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 174356-35-5 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 183238-59-7 Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-4-yl ester 
• 183238-60-0 Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-6-(2,4-dimethoxy-phenyl)-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 183238-61-1 Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-6-(4-methoxy-phenyl)-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 183238-64-4 4-(2-Amino-2-deoxy-β-D-glucopyranosyl)-1-methoxybenzene 
• 182003-15-2 4,5-dibromopentanyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1-4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 182003-19-6 pent-4-enyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1-4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 182003-09-4 pent-4-enyl 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 182003-00-5 pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 189218-66-4 pent-4-enyl (3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1->6)-3-O-benzoyl-4-O-benzyl-2-deoxy-2-(pent-4-enoylamino)-β-D-glucopyranoside 
• 217814-90-9 thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 217814-87-4 thexyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 217814-79-4 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl trichloroacetimidate 

Relevant articles and documents

N-Tetrachlorophthaloyl-Protected Trichloroacetimidate of Glucosamine as Glycosyl Donor in Oligosaccharide Synthesis

N-Tetrachlorophthaloyl (TCP) protection of glucosamine could be readily carried out with tetrachlorophthalic anhydride and then treatment with acetic anhydride in pyridine.Ensuing reaction with N2H4*HOAc and then base-catalyzed activation with trichloroac

Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride and its derivatives

2-Acetamido-2-deoxy-D-glucose hydrochloride (D-glucosamine hydrochloride) has been used for the preparation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β- (4) and 2-tetrachlorophthalimido-α,β-D-glucopyranose (6), which have been transformed into the appropriate bromides and the chloride. Both bromo and chloro sugars were used as a glycosyl donors for the glycosylation of diosgenin [(25R)-spirost-5-en-3β-ol]. These condensations were conducted under mild conditions, using silver triflate as a promoter, and gave diosgenyl glycosides 9 and 12. Each of them was converted into diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride (11) and N-acylamido derivatives. The structures of all new glycosides were established by 1H and 13C NMR spectroscopy. These diosgenyl glycosides are the first saponins containing the D-glucosamine residue that have been synthesized. These compounds show promising antitumor activities. The synthetic saponins increase the number of apoptotic B cells, in combination with cladribine (2-CdA), that are isolated from chronic lymphotic leukemia (B-CLL) patients.