Description

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose (CAS: 4132-28-9) is a highly specialized carbohydrate derivative extensively utilized in synthetic organic chemistry and glycoscience research. With the molecular formula C₃₄H₃₆O₆, this compound features a D-glucopyranose core fully protected by benzyl (phenylmethyl) groups at the 2, 3, 4, and 6 positions, rendering it a pivotal intermediate in the synthesis of complex oligosaccharides and glycoconjugates. Its structural integrity and high purity (≥98% by TLC) make it ideal for controlled glycosylation reactions, protecting-group strategies, and asymmetric synthesis. Available as a white to off-white crystalline powder, this reagent is characterized by its stability under anhydrous conditions and compatibility with a wide range of organic solvents. Researchers rely on its consistent performance in carbohydrate chemistry, medicinal chemistry, and materials science applications.

Properties

• CAS Number: 4132-28-9
• Complexity: 665
• IUPAC Name: (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-ol
• InChI: InChI=1S/C34H36O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-35H,21-25H2/t30-,31-,32+,33-,34?/m1/s1
• InChI Key: OGOMAWHSXRDAKZ-BKJHVTENSA-N
• Exact Mass: 540.25118886
• Molecular Formula: C34H36O6
• Molecular Weight: 540.6
• SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Topological: 66.4
• Monoisotopic Mass: 540.25118886
• Synonyms: 4132-28-9, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol, DTXSID001232816, 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-ol, DTXCID601664021, 609-908-7, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose, (3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-6-((BENZYLOXY)METHYL)TETRAHYDRO-2H-PYRAN-2-OL, D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-, (3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol, MFCD00066004, tetrabenzylglucose, TetraBn-Glu-OH, C34H36O6, 3GG5HR4KMM, SCHEMBL1793061, AC-772, 2,3,4,6-tetra-O-benzylglucopyranose, AKOS015896450, CS-W011467, HY-W010751, MT06691, (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol, 2,3,4,6-tetra-O-benzyl glucopyranose, 2,3,4,6-tetra-O-benzyl-glucopyranose, DS-10758, 2,3,4,6-terta-O-Benzyl-D-Glucopyranose, EN300-262955, A1-00201, a-D-Glucopyranose,2,3,4,6-tetrakis-O-(phenylmethyl)-, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose, >=98% (TLC), 2,3,4,6-Tetra-O-benzyl-D-glucopyranose, >=98.0% (TLC)

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose serves as a key building block in the synthesis of glycosides, glycopeptides, and other bioactive molecules. It is widely employed in protecting-group chemistry to prevent unwanted side reactions during multi-step synthetic processes. This compound is particularly valuable in the development of carbohydrate-based vaccines and drug delivery systems. Its versatility also extends to the preparation of chiral auxiliaries and ligands for asymmetric catalysis.

Safety and Hazards

GHS Hazard Statements

• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H413 (50%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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