Name: China Manufacturer Supply Methyl-2-deoxy-D-ribofuranoside diacetate CAS 151767-35-0
Brand: Wuhan Fortuna Chemical Co., Ltd.

Methyl-2-deoxy-D-ribofuranoside diacetate is a chemically modified derivative of 2-deoxy-D-ribose, a sugar central to DNA structure. Below is a detailed description of its properties and applications:

1. Chemical Structure

Core framework: A furanose ring (5-membered oxygen-containing ring) derived from D-ribose, with the hydroxyl group (-OH) at the C2 position replaced by hydrogen (hence "2-deoxy").
Substituents:
C1 position: Protected by a methyl group (-OCH₃) as a glycosidic bond.
C3 and C5 positions: Acetyl groups (-OAc) acting as hydroxyl-protecting groups.
Molecular formula: Typically C₁₀H₁₆O₆ (may vary slightly depending on synthesis).
Stereochemistry: Retains the D-configuration of natural ribose.

2. Key Properties

Protective groups:
The methyl group stabilizes the glycosidic bond at C1, preventing unwanted reactivity.
Acetyl groups shield hydroxyls at C3 and C5, enabling selective functionalization in subsequent reactions.
Solubility: Soluble in organic solvents (e.g., dichloromethane, THF) but poorly soluble in water.
Stability: Enhanced resistance to acidic/basic conditions and oxidation due to acetyl protection.

3. Synthesis

Starting material: Derived from 2-deoxy-D-ribose.
Key steps:
Methyl glycosidation: Reaction with methanol under acidic conditions (e.g., HCl) to form the methyl glycoside at C1.
Acetylation: Selective protection of hydroxyl groups at C3 and C5 using acetic anhydride (Ac₂O) or acetyl chloride (AcCl).

4. Primary Applications

Pharmaceutical intermediates:
Serves as a building block for nucleoside analogs (e.g., antiviral agents like acyclovir or anticancer drugs like gemcitabine).
Used in prodrug design, where acetyl groups are enzymatically cleaved to release active hydroxyl groups.
Organic synthesis:
A model compound for hydroxy protection strategies in carbohydrate chemistry.
Facilitates glycosylation reactions to construct complex glycans or modified sugars.
Biochemical research:
Acts as a substrate or inhibitor for enzymes like glycosidases or kinases.
Used to study nucleic acid metabolism or develop molecular probes.

5. Deprotection and Functionalization

Acetyl removal: Achieved via alkaline hydrolysis (e.g., NH₃/MeOH) or enzymatic cleavage.
Glycosidic bond cleavage: Acidic conditions (e.g., trifluoroacetic acid) can break the methyl glycoside to regenerate free hydroxyls for further modifications.

6. Example Use Cases

Anticancer drug synthesis: Key intermediate in producing gemcitabine, a chemotherapy agent targeting DNA replication.
DNA analog development: Used to synthesize modified deoxyribonucleotides for gene editing tools or molecular diagnostics.

For precise structural data, synthesis protocols, or literature references, consult specialized databases like SciFinder or Reaxys.