2,3,4,6-Tetra-O-benzoyl-D-mannopyranose

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose
• CAS No.: 113544-59-5
• Molecular Formula: C₃₄H₂₈O₁₀
• Molecular Weight: 596.59
• DSSTox Substance ID: DTXSID80921103
• Nikkaji Number: J1.200.663B
• Mol file: 113544-59-5.mol

Synonyms:2,3,4,6-Tetra-O-benzoyl-D-mannopyranose;113544-59-5;627466-98-2;[(2R,3R,4S,5S)-3,4,5-tribenzoyloxy-6-hydroxyoxan-2-yl]methyl benzoate;D-Mannose, 2,3,4,6-tetrabenzoate;SCHEMBL6219613;DTXSID80921103;MFCD02683399;2,3,4,6-Tetra-O-benzoylhexopyranose;AKOS027320098;2,3,4,6-tetra-O-benzoyl-mannopyranose;T2056;D92575;2-O,3-O,4-O,6-O-Tetrabenzoyl-D-mannopyranose;W-203335;(2R,3R,4S,5S)-2-(benzoyloxymethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property of 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose

Chemical Property:

• Melting Point: 182 °C
• Refractive Index: -78 ° (C=1, CHCl3)
• Boiling Point: 756.4±60.0 °C(Predicted)
• PKA: 12.60±0.20(Predicted)
• PSA: 142.50000
• Density: 1.316±0.06 g/cm3(Predicted)
• LogP: 4.08000
• Storage Temp.: Freezer
• Solubility.: slightly sol. in Chloroform
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 596.16824709
• Heavy Atom Count: 44
• Complexity: 959

Purity/Quality:

97% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzoyl-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@@H](C(O2)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose is a carbohydrate used for chelation-assisted glycosylation. 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose also appears in the synthesis of N-acetylglucosamine-bearing oleanolic acid saponins, which have anti-cancer properties towards human leukemia and colorectal cancer cells.

Technology Process of 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose

There total 6 articles about 2,3,4,6-Tetra-O-benzoyl-D-mannopyranose 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:

→ O2,O3,O4,O6-Tetrabenzoyl-D-mannose (113544-59-5)

Guidance literature:

With cadmium(II) carbonate; acetone; mercury dichloride;

DOI:10.1021/ja01292a010

Reference yield:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4) → O2,O3,O4,O6-Tetrabenzoyl-D-mannose (113544-59-5)

Guidance literature:

With acetone; silver carbonate;

DOI:10.1021/ja01161a091

Reference yield:

benzoyl chloride (98-88-4) → O2,O3,O4,O6-Tetrabenzoyl-D-mannose (113544-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 1,2-dichloro-ethane; acetic acid; hydrogen bromide

3: Ag₂CO₃; aqueous acetone

With pyridine; hydrogen bromide; acetic acid; 1,2-dichloro-ethane; acetone; silver carbonate;

DOI:10.1021/ja01161a091

upstream raw materials:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

benzoyl chloride

1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose