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| Other Sizes |
| Targets |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose does not have a biological target; it is a chemical building block. Its "target" in synthetic chemistry is the activation of the anomeric position for glycosylation reactions. The benzyl protecting groups are stable under a wide range of reaction conditions but can be removed by hydrogenolysis (e.g., Pd/C, H2) to yield free glucose derivatives. The free hemiacetal at C1 can be converted into a glycosyl bromide, trichloroacetimidate, or other leaving group for stereoselective glycosidic bond formation.
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| ln Vitro |
No direct biological activity of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose has been reported because it is a synthetic intermediate. However, after deprotection, the resulting glucose derivatives (e.g., D-glucuronic acid conjugates) may have biological activities. For example, glucuronide metabolites of drugs are often inactive and excreted. The compound itself is used in vitro to demonstrate glycosylation reactions; its activity is measured by conversion yield in a chemical reaction, not by cell-based assays. It has no agonistic or antagonistic effects on enzymes or receptors.
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| ln Vivo |
There is no in vivo activity for this compound as a drug, as it is not administered to animals for therapeutic purposes. However, it is used in the synthesis of drug candidates that are later tested in vivo. For instance, a glycosylated natural product analog synthesized using this benzyl-protected glucose may be evaluated in mouse xenograft models for anticancer activity. The protective groups are removed at the final step to yield the active compound. Thus, the role of this compound is strictly in the chemical synthesis phase, not in biological testing.
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| Enzyme Assay |
The purity of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is determined by non-cellular analytical methods such as high-performance liquid chromatography (HPLC) on a normal-phase column with UV detection at 254 nm (benzyl groups absorb strongly). Thin-layer chromatography (TLC) using silica gel and a solvent system of ethyl acetate/hexane (e.g., 1:3) gives an Rf value typically around 0.3-0.5. The anomeric configuration (alpha/beta ratio) can be determined by ¹H NMR (the anomeric proton appears as a doublet at delta ~5.1 ppm for alpha-anomer and ~4.4 ppm for beta-anomer with coupling constants J1,2 of ~3.5 Hz and ~7.5 Hz, respectively). Mass spectrometry (ESI-MS) confirms the molecular ion [M+Na]+ at m/z 561.2.
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| Cell Assay |
This compound is not used in cell-based assays because it is insoluble in aqueous media and the benzyl groups are not compatible with living cells (they could be metabolized to benzyl alcohol, which is toxic). However, after deprotection to free glucose, the product can be used in cell uptake or metabolic studies. For example, tritium-labeled glucose is used to measure glucose transport in cultured adipocytes or hepatocytes. Such assays are performed in Krebs-Ringer buffer, with cells incubated with labeled glucose for 5-30 minutes, then washed and lysed, and radioactivity counted. The benzylated compound is not part of this protocol.
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| Animal Protocol |
In vivo animal experiments are not performed with this protected sugar because it is not bioavailable and may be toxic. Instead, the final deprotected glycoside product may be tested. For instance, a novel glucuronide prodrug synthesized from this intermediate is administered orally to rats. Blood samples are collected at various time points, and the concentration of the active drug and its glucuronide metabolite is measured by LC-MS/MS. The prodrug approach is designed to improve solubility or target delivery. The benzylated glucose intermediate is never directly administered.
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| ADME/Pharmacokinetics |
This compound is a chemical intermediate and has no pharmacokinetic profile. However, if one were to consider its potential oral absorption, the high lipophilicity due to four benzyl groups (cLogP ~5-6) would suggest good membrane permeability, but the compound would likely be extensively metabolized by debenzylation in the liver (by cytochrome P450 enzymes) to generate benzyl alcohol (toxic) and free glucose. In practice, this compound is not suitable for in vivo use. The final deprotected glucuronide metabolites of drugs typically have short half-lives (2-6 h) and are excreted renally.
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| Toxicity/Toxicokinetics |
The toxicity of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is not well documented, but as a benzyl ether, it may be irritating to skin and eyes. Benzyl alcohol, a potential metabolite, has known toxicity (LD50 rat oral ~1230 mg/kg) and can cause respiratory depression, metabolic acidosis, and vasodilation. Handle with care: use fume hood, gloves, and goggles. This compound is not classified as a dangerous substance under GHS for acute oral toxicity, but standard laboratory chemical precautions apply. No specific long-term toxicity studies have been performed because it is not intended for human exposure.
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| References | |
| Additional Infomation |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose (CAS 4132-28-9) has molecular formula C34H3₆O₆ and molecular weight 540.65 g/mol. It is a white to off-white crystalline powder with melting point 80-84degC. It is soluble in dichloromethane, chloroform, ethyl acetate, and toluene, but insoluble in water. This compound is a key intermediate in carbohydrate chemistry, used in the synthesis of glycosphingolipids, heparan sulfate fragments, and natural product glycosides. It is not a drug and has no clinical trials or FDA approval. The product is for research use only.
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| Molecular Formula |
C34H36O6
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|---|---|
| Molecular Weight |
540.66
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| Exact Mass |
540.251
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| CAS # |
4132-28-9
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| PubChem CID |
54149221
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| Appearance |
Solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
672.4±55.0 °C at 760 mmHg
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| Melting Point |
145-149ºC
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| Flash Point |
360.4±31.5 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.619
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| LogP |
9.05
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
40
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| Complexity |
665
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1C([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])OC([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])OC([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])OC([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])OC([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])O[H]
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| InChi Key |
OGOMAWHSXRDAKZ-GYLADCCPSA-N
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| InChi Code |
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+/m0/s1
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| Chemical Name |
(2R,3S,4R,5S,6S)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
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| Synonyms |
2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8496 mL | 9.2480 mL | 18.4959 mL | |
| 5 mM | 0.3699 mL | 1.8496 mL | 3.6992 mL | |
| 10 mM | 0.1850 mL | 0.9248 mL | 1.8496 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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