Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

Base Information

• Chemical Name: Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside
• CAS No.: 3554-96-9
• Molecular Formula: C21H31 N O11
• Molecular Weight: 473.47
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID30415340
• Nikkaji Number: J1.693.137C
• Wikidata: Q27127150
• Metabolomics Workbench ID: 61026
• Mol file: 3554-96-9.mol

Synonyms:3554-96-9;Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside;beta-D-Gal-(1->3)-alpha-D-GalNAc-OBn;beta-D-Galp-(1->3)-alpha-D-GalpNAc-OBn;N-[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-phenylmethoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide;Benzyl 2-acetamido-2-deoxy-3-O-(b-D-galactopyranosyl)-a-D-galactopyranoside;Benzyl 2-acetamido-2-deoxy-3-O-(B-D-galactopyranosyl)A-D-galactopyranoside;Benzyl 2-Acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl) alpha-D-galactopyranoside;benzyl beta-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-alpha-D-galactopyranoside;1jlx;Galbeta1-3GalNAcalphaOBn;SCHEMBL542353;CHEBI:60241;DTXSID30415340;Benzyl 2-Acetamido-2-deoxy-3-O-(|A-D-galactopyranosyl) |A-D-galactopyranoside;AS-73040;CS-0226084;beta-D-Gal-(1->3)-alpha-D-GalNAc-1->OCH2Ph;W-202463;Q27127150;Benzyl 2-acetamido-2-deoxy-3-O--D-galactopyranosyl--D-galactopyranoside;N-Acetyl-1-O-benzyl-3-O-beta-D-galactopyranosyl-alpha-D-galactosamine;Benzyl 2-acetamido-2-deoxy-3-O- beta -D-galactopyranosyl- alpha -D-galactopyranoside;Benzyl 2-acetamido-2-deoxy-3-O-|A-D- galactopyranosyl-|A-D-galactopyranoside;Benzyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-alpha-D-galactopyranoside, Min. 98%;N-((2S,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl)acetamide;N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

Chemical Property of Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

Chemical Property:

• Melting Point: 218-220°C
• Refractive Index: 1.624
• PSA: 187.40000
• LogP: -2.63800
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 473.18971080
• Heavy Atom Count: 33
• Complexity: 619

Purity/Quality:

98%Min ^*data from raw suppliers

Benzyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)CO)O)OC3C(C(C(C(O3)CO)O)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[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O
• Uses: A substrate for N-acetyl-?D-glucosaminyltransferase. Also an inhibitor of 1-?3-galctotransferase Benzyl 2-AcetaMido-2-deoxy-3-O-(β-D-galactopyranosyl) α-D-galactopyranoside is useful as a substrate for UDP-GlcNAc:Gal1-beta-3GalNAc(GlcNAc-GalNAc)-6-beta-GlcNAc transferase and sialytransferase.

Technology Process of Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

There total 10 articles about Benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside 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: 62.0%

benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (3554-93-6,347411-88-5) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → (2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-O-benzyl glycoside (3554-96-9) + Galβ1→6GalNAcα-Bn (93496-44-7)

Guidance literature:

With sodium phosphate; β-galactosidase; In water; N,N-dimethyl-formamide; at 37 ℃; for 3h; Product distribution; effect of donor/acceptor ratio, also immobilized β-galactosidase;

DOI:10.1271/bbb.62.1313

Reference yield:

benzyl 2-acetamide-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside (117182-56-6) → (2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-O-benzyl glycoside (3554-96-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 57.5 percent / mercuric cyanide / benzene; nitromethane / 72 h / Ambient temperature

2: 81.4 percent / M sodium methoxide / methanol / 5 h / Ambient temperature

3: 81.9 percent / zinc chloride / Ambient temperature

4: 78.9 percent / pyridine / 48 h / Ambient temperature

5: 85.5 percent / 60percent aq. acetic acid / 0.67 h / 98 °C

6: sodium methoxide / methanol

With pyridine; sodium methylate; acetic acid; zinc(II) chloride; mercury(II) cyanide; In methanol; nitromethane; benzene;

DOI:10.1016/0008-6215(84)85130-7

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-O-benzyl glycoside (3554-96-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 57.5 percent / mercuric cyanide / benzene; nitromethane / 72 h / Ambient temperature

2: 81.4 percent / M sodium methoxide / methanol / 5 h / Ambient temperature

3: 81.9 percent / zinc chloride / Ambient temperature

4: 78.9 percent / pyridine / 48 h / Ambient temperature

5: 85.5 percent / 60percent aq. acetic acid / 0.67 h / 98 °C

6: sodium methoxide / methanol

With pyridine; sodium methylate; acetic acid; zinc(II) chloride; mercury(II) cyanide; In methanol; nitromethane; benzene;

DOI:10.1016/0008-6215(84)85130-7

upstream raw materials:

benzyl 2-acetamido-2-deoxy-3-O-(2,3-di-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside

4-nitrophenyl-β-D-galactopyranoside

benzyl 2-acetamide-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

Downstream raw materials:

benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Refernces

• 1、 Naundorf, Andreas,Caussette, Mylene,Ajisaka, Katsumi. "Characterization of the Immobilized β-Galactosidase C from Bacillus circulans and the Production of β(1→3)-linked Disaccharides". . p. 1313 - 1317. Retrieved 1998.
• 2、 -. "Fibrinogen-coated particles for therapeutic use". . . Retrieved 2008/06/13.