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Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside

Cat No.:V58638 Purity: ≥98%
Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside is the enantiomer of Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside.
Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside
Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside Chemical Structure CAS No.: 20672-63-3
Product category: Others 12
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes
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Product Description
Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside is the enantiomer of Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside. Methyl 2,3-O-Isopropylidene-β-L-ribofuranoside is an analogue of L-ribose.
Methyl 2,3-O-Isopropylidene-beta-L-ribofuranoside is a protected carbohydrate derivative. It is an important intermediate in the chemical synthesis of L-nucleosides, which are building blocks for antiviral and anticancer drugs such as L-deoxythymidine and L-ribavirin.
Biological Activity I Assay Protocols (From Reference)
Targets
This compound is not a drug and does not have a pharmacological target. It is a synthetic intermediate used in organic chemistry. Its role is to serve as a chiral building block for constructing nucleoside analogues that target viral polymerases or cellular kinases.
ln Vitro
No direct in vitro activity as this is a synthetic intermediate. However, the final L-nucleoside products derived from this intermediate exhibit antiviral activity against hepatitis B virus (HBV), hepatitis C virus (HCV), and HIV by inhibiting viral reverse transcriptase or RNA-dependent RNA polymerase.
ln Vivo
No direct in vivo activity for the intermediate itself. The L-nucleosides synthesized from it, such as L-deoxythymidine, have shown in vivo efficacy in animal models of viral infection, reducing viral load and improving liver histology without significant mitochondrial toxicity.
Enzyme Assay
Not applicable. For related L-nucleosides, standard assays involve measuring inhibition of viral polymerases using purified enzyme, template/primer, and radiolabeled nucleotides. The compound is added at various concentrations, and incorporated radioactivity is quantified by filter binding.
Cell Assay
Not applicable for this intermediate. For derived L-nucleosides, cellular assays use HBV-infected HepG2.2.15 cells or HCV replicon cells. Cells are treated with the compound for several days, and viral DNA/RNA is quantified by real-time PCR or Southern blot.
Animal Protocol
Not applicable for this intermediate. For L-nucleosides, in vivo studies use HBV-transgenic mice or woodchuck hepatitis virus models. The compound is administered orally or intraperitoneally, and serum viral DNA levels are monitored by PCR over 2-4 weeks.
ADME/Pharmacokinetics
Pharmacokinetic data are not relevant for this synthetic intermediate. For L-nucleoside drugs, they typically have good oral bioavailability, are converted intracellularly to active triphosphates, and have half-lives of several hours in plasma.
Toxicity/Toxicokinetics
The intermediate is a chemical reagent and is handled with standard laboratory precautions. It is not intended for in vivo use. The L-nucleoside products have improved toxicity profiles compared to D-nucleosides, showing reduced mitochondrial toxicity and lower risk of lactic acidosis.
References

[1]. Enantiomerically pure 7‐oxabicylo[2.2.1]hept‐5‐en‐zyl derivatives as synthetic intermediates. Part III. Total synthesis of D‐ and L‐ribose derivatives.

Additional Infomation
This compound is solely a research chemical for organic synthesis. It has no clinical trials or approved status. It is commonly used in the preparation of L-configured nucleoside analogues, which are of interest for antiviral drug development due to their resistance to host nucleoside metabolizing enzymes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H16O5
Molecular Weight
204.22
Exact Mass
204.099
CAS #
20672-63-3
Appearance
Colorless to light yellow liquid
LogP
-0.4
SMILES
CC1(O[C@H]2[C@@H](O[C@@H]([C@H]2O1)OC)CO)C
InChi Key
DXBHDBLZPXQALN-XAMCCFCMSA-N
InChi Code
InChI=1S/C9H16O5/c1-9(2)13-6-5(4-10)12-8(11-3)7(6)14-9/h5-8,10H,4H2,1-3H3/t5-,6-,7-,8-/m0/s1
Chemical Name
[(3aS,4S,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (489.67 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (12.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8967 mL 24.4834 mL 48.9668 mL
5 mM 0.9793 mL 4.8967 mL 9.7934 mL
10 mM 0.4897 mL 2.4483 mL 4.8967 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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