10385-50-9

Usage

Uses

Used in Pharmaceutical Industry:
1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose is used as a precursor in the synthesis of pharmaceutical compounds for its enhanced stability and resistance to degradation, allowing for the development of more effective and potent drugs.
Used in Chemical Synthesis:
1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose is used as a building block in the synthesis of other complex organic compounds, leveraging its unique structure and functional groups for the creation of novel molecules with potential applications in various fields.
Used in Research and Development:
1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose serves as a valuable compound in research settings, where its unique properties can be explored for new applications, understanding its interactions with biological systems, and developing new methods for its synthesis and modification.

Upstream product

• 108-24-7 acetic anhydride 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 64-19-7 acetic acid 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 10036-64-3 N-acetyl-D-glucosamine 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 75-36-5 acetyl chloride 
• 10387-40-3 potassium thioacetate 
• 14131-68-1 N-acetyl-D-glucosamine 
• 61259-49-2 2,3,4,6-tetra-O-acetyl-D-gluconic acid 
• 7597-81-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 
• 51471-40-0 6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol 

Downstream Products

• 13089-27-5 p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 72333-19-8 propyl 2-acetamido-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 84218-49-5 O-(N-acetamido-2-tri-O-acetyl-3,4,6-desoxy-2-β-D-glucopyranosyl)-4-O-acetyl-1-tri-O-benzyl-2,3,5-D-ribitol 
• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10294-12-9 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 155197-37-8 n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 135198-09-3 octadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of staphylococcus aureus type 5 trisaccharide repeating unit: Solving the problem of lactamization

The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging α-fucosylation and β-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a β-d-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.

Synthesis of a Difunctional Orthogonal Coupler for the Preparation of Carbohydrate-Functionalized sP(EO-stat-PO) Hydrogels

The synthesis and characterization of a new difunctional coupler (4) based on trimethylolpropane (TMP) are described. The coupler is used to connect biologically active N-acetylglucosamine (GlcNAc) on amino-reactive microtiter plates and on star-shaped po

A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine

Synthetic approaches towards N-acetylgalactosamine (GalNAc) have been attracting considerable interest since this compound is known for its pivotal role in cell-cell interaction and receptor induced cell signaling. Herein, we present a synthetic route in which two of the four stereogenic centers present in the target compound are derived from enantiopure tartaric acid being selectively converted to epoxy alcohols. The key step is the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).

Conversion of 2-Acetamido-2-deoxy-β-D-glucopyranose (N-Acetylglucosamine) into 2-Acetamido-2-deoxy-β-D-galactopyranose (N-Acetylgalactosamine) Using a Biotransformation to Generate a Selectively Deprotected Substrate for SN2 Inversion

A procedure is described for the conversion of N-acetylglucosamine 2 into N-acetylgalactosamine 1, in which use is made of a 4,6-acetyl migration in a precursor selectively deprotected by a biotransformation procedure.

Tetranuclear zinc cluster: A dual purpose catalyst for per-: O -acetylation and de- O -acetylation of carbohydrates

The trifluoroacetic acid adduct of tetranuclear zinc cluster Zn4(OCOCF3)6O catalysis in per-O-acetylation and de-O-acetylation of carbohydrates at 70 °C can be tuned by adjusting the reaction medium. Per-O-acetylation of hexopyranoses with a near stoichiometric amount of acetic anhydride in toluene resulted in the exclusive formation of pyranosyl products as an anomeric mixture, whereas de-O-acetylation of acetates occurred in methanol in high yields. In the latter, methanol acts as both nucleophile and solvent, and the reaction conditions were compatible to acid- and base-sensitive groups and amino acid derivatives.

I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation

A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG400-based ionic liquid catalyst (I2/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I2/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.

Solvent-free per-O-acetylation of carbohydrates

A facile, solvent-free acetylation method promoted by commercial 4? molecular sieves is described here for the synthesis of per-Oacetylated carbohydrates, which are important intermediates in carbohydrate chemistry. Several examples of carbohydrate and noncarbohydrate substrates are provided.

Exploring the interactions of unsaturated glucuronides with influenza virus sialidase

A series of C3 O-functionalized 2-acetamido-2-deoxy-4-β-d- glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-μM level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

Synthesis of methyl 2-acetamido-2-deoxy-1-seleno-β-D-gluco- And galacto-pyranoside: Selenium metabolites in human urine

An efficient synthesis of two methyl 2-acetamido-2-deoxy-1-seleno-β-D-hexopyranosides is reported. The synthesized compounds, which have recently been identified in human urine, will be used in further studies on the metabolism and toxicology of selenium.

Reducing oligosaccharides via glycal assembly: On the remarkable stability of anomeric hydroxyl groups to global deprotection with sodium in liquid ammonia

Several partially benzylated 1-hydroxy sugars were rapidly deprotected by sodium/liquid ammonia. The terminal hemiketal linkage of the substrates remained intact under these conditions and does not generate ring-opened alditols. Peracetylated glucose and glucosamine derivatives were obtained in 64-79% isolated yields.