CAS 60431-34-7

2,3,4-Tri-O-benzyl-L-fucopyranose

Description:

2,3,4-Tri-O-benzyl-L-fucopyranose is a fucosylated carbohydrate derivative characterized by the presence of three benzyl groups attached to the hydroxyl positions at the 2, 3, and 4 positions of the fucopyranose ring. This compound is a derivative of L-fucose, a naturally occurring sugar that plays a significant role in various biological processes, including cell recognition and signaling. The benzyl groups enhance the lipophilicity and stability of the molecule, making it useful in organic synthesis and as a potential building block in glycosylation reactions. The compound typically exhibits a white to off-white crystalline appearance and is soluble in organic solvents such as dichloromethane and methanol, but less soluble in water due to its hydrophobic nature. Its structure can be confirmed through techniques such as NMR spectroscopy and mass spectrometry. Additionally, 2,3,4-Tri-O-benzyl-L-fucopyranose may have applications in the development of glycosylated drugs and in the study of carbohydrate-protein interactions.

Formula: C₂₇H₃₀O₅

InChI: InChI=1/C27H30O5/c1-20-24(29-17-21-11-5-2-6-12-21)25(30-18-22-13-7-3-8-14-22)26(27(28)32-20)31-19-23-15-9-4-10-16-23/h2-16,20,24-28H,17-19H2,1H3/t20-,24+,25+,26-,27-/m0/s1

Synonyms:

• 2,3,4-tri-O-benzyl-6-deoxy-alpha-L-galactopyranose
• 2,3,4-tri-O-benzyl-6-deoxy-beta-L-galactopyranose

(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

CAS: 60431-34-7

Formula: C₂₇H₃₀O₅

Purity: 95%

Color and Shape: Solid

Molecular weight: 434.5241

Ref: IN-DA00E9H1

2,3,4-Tri-O-benzyl-L-fucopyranose

CAS: 60431-34-7

Ref: 7W-GC2256

2,3,4-Tri-O-benzyl-L-fucopyranose

CAS: 60431-34-7

2,3,4-Tri-O-benzyl-L-fucopyranose is a synthetic compound that activates the selectin receptor on the surface of white blood cells. It has been shown to activate the cell surface receptors for the lectin mannose and mannose-binding protein which are involved in the recognition of pathogens. 2,3,4-Tri-O-benzyl-L-fucopyranose is also able to inhibit magnesium ion binding to its target site on the bacterial surface. This inhibition prevents bacteria from attaching themselves to host tissues or other cells by binding with these sites. The compound was synthesized by a stereoselective method using silver trifluoromethanesulfonate as an activating reagent and can be used as an antimicrobial agent in mammals.

Formula: C₂₇H₃₀O₅

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 434.52 g/mol

Ref: 3D-MT06626

2,3,4,-Tri-O-benzyl-L-fucopyranose

Controlled Product

CAS: 60431-34-7

Applications An intermediate used for the preparation of selectin blockers and other oligosaccharides
References Susaki, H., et al.: Chem. Pharm. Bull., 42, 1917 (1994), Kiyoi, T., et al.: Bioorg. Med. Chem. Lett., 8, 2845 (1998),

Formula: C₂₇H₃₀O₅

Color and Shape: Neat

Molecular weight: 434.52

Ref: TR-T768000