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

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

Used in Pharmaceutical Industry:
2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-Dis used as an intermediate in the synthesis of N-Acetylchitooctaose (A168460), a chitooligosaccharide that activates Saccharomyces cerevisiae chitin biosynthesis. 2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-Dhas potential applications in human therapy for cancer treatment, particularly in colon cancer and melanoma.
Used in Cancer Treatment:
2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-Dis used as a precursor for the development of chitooligosaccharides with affinity for NKR-P1A protein, which is the major activating receptor on the surface of rat natural killer (NK) cells. This interaction may enhance the immune response against cancer cells and contribute to the development of novel cancer treatment strategies.
Used in Chitin Biosynthesis:
2-DEOXY-2-(TETRACHLOROPHTHALIMIDO)-Dplays a role in the synthesis of N-Acetylchitooctaose, which activates chitin biosynthesis in Saccharomyces cerevisiae. This process is essential for the growth and development of various organisms and may have implications in the study of cellular processes and the development of new therapeutic approaches.

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 
• 207863-38-5 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester 
• 217814-68-1 1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside 
• 286018-83-5 phenyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 217814-69-2 phenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 217814-73-8 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 
• 217814-88-5 C₄₆H₅₅Cl₄NO₁₃Si 
• 217814-89-6 C₄₆H₅₅Cl₄NO₁₃Si 
• 217814-74-9 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 
• 217814-86-3 C₄₃H₅₃Cl₄NO₁₆Si 
• 217814-71-6 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 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 
• 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 
• 217814-90-9 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 

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

Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside

Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d- glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-d- glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice.

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.