Benzyl-alpha-galnac

Base Information

• Chemical Name: Benzyl-alpha-galnac
• CAS No.: 3554-93-6
• Molecular Formula: C15H21NO6
• Molecular Weight: 311.335
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID101293813
• Nikkaji Number: J642.119I
• Mol file: 3554-93-6.mol

Synonyms:benzyl N-acetyl-alpha-D-galactosaminide;benzyl-alpha-GalNAc;benzyl-alpha-N-acetylgalactosamine;Bz-alpha-GalNAc;GalNAc-alpha-O-benzyl

Chemical Property of Benzyl-alpha-galnac

Chemical Property:

• Vapor Pressure: 5.36E-15mmHg at 25°C
• Melting Point: 201-203°C
• Refractive Index: 1.59
• Boiling Point: 594.9 °C at 760 mmHg
• PKA: 12.98±0.70(Predicted)
• Flash Point: 313.6 °C
• PSA: 108.25000
• Density: 1.34 g/cm³
• LogP: -0.46220
• Storage Temp.: −20°C
• Solubility.: methanol: soluble10mg/mL, clear
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 311.13688739
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Benzyl 2-acetamido-2-deoxy-a-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1OCC2=CC=CC=C2)CO)O)O
• Uses: A substrate for N-acetyl-?-D-glucosaminyltransferase. Also an inhibitor of 1-?-3-galctotransferase. Blocks the apical biosynthetic pathway in polarized HT-29 cells.

Technology Process of Benzyl-alpha-galnac

There total 48 articles about Benzyl-alpha-galnac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8) → benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5)

Guidance literature:

With methanol; sodium methylate; at 20 ℃;

DOI:10.1021/ja020627c

Reference yield: 81.6%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5)

Guidance literature:

With acetyl chloride; In methanol; at 20 - 25 ℃; for 24h; Cooling with ice;

Reference yield: 80.0%

N-acetyl-D-galactosamine (72-87-7,1136-42-1,1136-44-3,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4,6082-29-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (3554-93-6,347411-88-5)

Guidance literature:

With acetyl chloride; at 60 ℃;

DOI:10.1074/jbc.M115.680470

upstream raw materials:

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yl ester

N-Acetyl-D-glucosamine

benzyl alcohol

Downstream raw materials:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-(diphenyl phosphate)

benzyl 2-acetamido-6-bromo-2,6-dideoxy-β-D-glucopyranoside

Refernces

SYNTHESYS OF BENZYL 2,3,4-TRI-ACETAMIDO-2,3,4,6-TETRADEOXY-α-D-GALACTOAYRANOSIDE

10.1016/0008-6215(83)88099-9

The research aimed to synthesize benzyl 2,3,4-tri-acetamido-2,3,4,6-tetradeoxy-α-D-galactopyranoside, a compound with D-galacto configuration, which was required for other work in the laboratory. The synthesis process involved several steps, starting with the treatment of benzyl 2-acetamido-2-deoxy-α-D-allopyranoside with methanesulfonyl chloride in pyridine to produce a tri-O-mesyl derivative. This was then reduced with sodium borohydride to form benzyl 2-acetamido-2,6-dideoxy-3,4-di-O-methylsulfonyl-α-D-allopyranoside. Further transformations through catalytic reduction and N-acetylation led to the target compound. The process also included the removal of the aglycon from the synthesized compound to obtain the alditol, which was then reduced and acetylated. The conclusions were supported by the 'H-n.m.r. and 13C-n.m.r. spectra, which confirmed the structure of the synthesized compounds, and the mass spectrum of the final product, which showed a single peak, indicating the successful synthesis of the desired compound.