2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose
• CAS No.: 22554-70-7
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.307
• DSSTox Substance ID: DTXSID30451925
• Nikkaji Number: J1.346.470G
• Wikidata: Q82272226
• Mol file: 22554-70-7.mol

Synonyms:2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose;22554-70-7;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate;SCHEMBL133581;DTXSID30451925;IEOLRPPTIGNUNP-HTOAHKCRSA-N;2,3,4,6-tetra-O-acetyl-alpha-D-galactose;2-O,3-O,4-O,6-O-Tetraacetyl-alpha-D-galactopyranose

Chemical Property of 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose

Chemical Property:

• Melting Point: 132-133 °C(Solv: ethanol (64-17-5))
• Boiling Point: 425.0±45.0 °C(Predicted)
• PKA: 11.44±0.70(Predicted)
• PSA: 134.66000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: -0.93820
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 348.10564683
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

99%min. ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)O)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose

There total 259 articles about 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranose 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%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 55 ℃; for 0.25h;

DOI:10.1016/S0040-4039(99)01558-0

Reference yield: 100.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With pyridine; dmap; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201701620

Reference yield: 99.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With water; silver carbonate; In acetone; for 0.5h;

DOI:10.1016/0008-6215(92)80015-S

upstream raw materials:

tetra-O-acetyl-N-p-tolyl-β-D-glucopyranosylamine

tetra-O-acetyl-N-p-tolyl-β-D-galactopyranosylamine

N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine

tetra-O-acetyl-N-(4-nitro-phenyl)-β-D-galactopyranosylamine

Downstream raw materials:

α,β-Trehaloseoctaacetat

6-<4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl>-5,6-dihydro-2H-pyran-2-on

6-<4-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyloxy)phenyl>-5,6-dihydro-2H-pyran-2-on

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide

Refernces

• 1、 -. "Mannose-modified azide exosome and application thereof". Paragraph 0056; 0062; 0065. . Retrieved 2021/06/23.
• 2、 Boltje, Thomas J.,Eerden, Nienke,Lefeber, Dirk J.,Merx, Jona,Noga, Marek J.,Pijnenborg, Johan F. A.,Rossing, Emiel,Titulaer, Willem H. C.,Veizaj, Raisa,White, Paul B.. "Fluorinated rhamnosides inhibit cellular fucosylation". . . Retrieved 2021/12/13.