2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
• CAS No.: 4132-28-9
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.656
• Hs Code.: 29400090
• European Community (EC) Number: 609-908-7,432-870-6
• DSSTox Substance ID: DTXSID001232816
• Nikkaji Number: J338.547G
• Wikidata: Q106890823
• Mol file: 4132-28-9.mol

Synonyms:4132-28-9;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;tetrabenzylglucose;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-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;(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;MFCD00066004;C34H36O6;SCHEMBL1793061;AMY8984;OGOMAWHSXRDAKZ-BKJHVTENSA-N;DTXSID001232816;AC-772;2,3,4,6-tetra-O-benzylglucopyranose;AKOS015896450;CS-W011467;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;A25206;EN300-262955;2-O,3-O,4-O,6-O-Tetrabenzyl-D-glucopyranose;2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose;A1-00201;J-620002;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);3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol

Chemical Property of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Chemical Property:

• Appearance/Colour: White crystaline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 145-149 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 672.378 °C at 760 mmHg
• PKA: 11.87±0.70(Predicted)
• Flash Point: 360.441 °C
• PSA: 66.38000
• Density: 1.222 g/cm³
• LogP: 5.67660
• Storage Temp.: −20°C
• Solubility.: Soluble in chloroform
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 540.25118886
• Heavy Atom Count: 40
• Complexity: 665

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric 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
• General Description: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a protected form of D-glucopyranose where all four hydroxyl groups (positions 2, 3, 4, and 6) are benzylated. In the study, it serves as a substrate for oxidation using iodine monochloride (ICl) under optimized conditions (1.5 equiv ICl, 3 equiv Cs2CO3, CH2Cl2, 0°C to RT), demonstrating its utility in alcohol oxidation reactions. The method efficiently converts it to the corresponding carbonyl compound, highlighting its role as a model compound for evaluating oxidative transformations in carbohydrate chemistry. The findings suggest its compatibility with mild, high-yielding oxidation protocols, making it valuable for synthetic applications.

Technology Process of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

There total 299 articles about 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 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%

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

Reference yield: 100.0%

2,3,4,6-tetra-O-benzyl-1-O-propynyl-D-glucopyranoside → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With water; gold(III) chloride; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1021/ja062425c

Reference yield: 100.0%

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

2-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrimidine

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2-pyridinecarboxylate

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2-pyridinecarboxylate

2-(2,3,4,6-tetra-O-benzyl-D-glycero-D-gulo-hexitol-1-yl)pyrrole

Refernces

Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates

10.1002/chem.201804416

The study, authored by Nicola Lucchetti and Ryan Gilmour, presents a novel approach to chemical glycosylation, which is a critical process in the synthesis of carbohydrates. It introduces a direct, metal-free method for the anomeric O-arylation of unactivated carbohydrates, bypassing the need for pre-functionalization of the substrate. This method employs stable aryliodonium salts to facilitate a formal O?H functionalization reaction at ambient temperature, leading to the formation of acetals directly from reducing sugars. The research demonstrates the process's efficiency and stereoretention with various monosaccharides, disaccharides, and trisaccharides, including those with fluorinated substrates to enhance the anomeric effect. The method's scalability is also validated, and it is suggested that this strategy could be broadly applicable for constructing complex acetals in carbohydrate chemistry.

Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds

10.1080/00397911.2015.1005630

The research investigates the use of iodine monochloride (ICl) as a highly efficient and green oxidant for converting alcohols to corresponding carbonyl compounds, aiming to find a cheap, mild, and high-yield oxidizing method for large-scale synthesis. The study optimizes reaction conditions using 2,3,4,6-tetra-O-benzyl-D-glucopyranose as the substrate, finding that 1.5 equivalents of ICl added dropwise in CH2Cl2 solution at 0°C to room temperature, with 3 equivalents of Cs2CO3 as the base in CH2Cl2 solvent, yields the best results. The optimized ICl/Cs2CO3 system is then tested on various alcohol substrates, successfully oxidizing aldose hemiacetals, diarylmethanols, arylalkylmethanols, and dialkylmethanols to their corresponding carbonyl compounds with short reaction times and high yields, but failing with olefin-bearing and primary alcohols. The research concludes that ICl is a superior alternative to the I2/K2CO3 system, offering less oxidant quantity, shorter reaction times, and higher yields, thus providing a greener and more efficient oxidation method for the studied alcohol substrates.