Production Method 1

15186-48-8

701-99-5

533-67-5

Reaction Conditions

1.1C:SnF2, S:DMF, S:Dimethylimidazolidinone, 25°C
2.1R:NH4OH, S:H2O
3.1R:AcOH, S:H2O
4.1R:Me2S, R:O3

Reference

Tin(II) fluoride

By Weigel, Leland O., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, From e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-3

Production Method 2

867-13-0

97-67-6

1125-88-8

100-51-6

110-87-2

533-67-5

Reaction Conditions

1.1R:BH3-Me2S, R:(MeO)3B, S:THF, 40 min, 0°C; 0°C → rt; 7 h, rt
1.2R:MeOH, rt
1.3C:p-MeC6H4SO3H, S:CH2Cl2, 24 h, rt
1.4R:Et3N, rt
2.1R:DMSO, R:Cl(O=)CC(=O)Cl, S:CH2Cl2, 15 min, -78°C
2.2S:CH2Cl2, 20 min, -78°C
2.3R:Et3N, -78°C; -78°C → rt; 20 min, rt
2.4R:NaH, S:THF, 30 min, 0°C; 0°C → -78°C
2.5S:THF, -78°C; -78°C → rt; 1 h, rt
3.1R:AlH(Bu-i)2, S:THF, S:Me(CH2)4Me, 30 min, -78°C; 15 min, -78°C
3.2R:Na2SO4, S:H2O
4.1C:p-MeC6H4SO3H, S:CH2Cl2, 5 min, 0°C; 0°C → rt; 25 min, rt
4.2R:NaHCO3, S:H2O, rt
5.1R:AlH(Bu-i)2, S:PhMe, S:Me(CH2)4Me, 10 min, 0°C; 2 h, 0°C; 0°C → rt; 1 h, rt
5.2R:Na2SO4, S:H2O, rt
6.1R:Martin's reagent, S:CH2Cl2, 0°C; 0°C → rt; 1 h, rt; cooled; 0°C; 0°C → rt; 1 h, rt
6.2R:Na2S2O3, S:H2O, rt
7.1C:PdCl2(CH3CN)2, S:THF, 1 h, rt
8.1R:NaIO4, R:2,6-Lutidine, C:OsO4, S:H2O, S:t-BuOH, S:Dioxane, 16 h, rt
8.2R:NaBH4, S:MeOH, 30 min, rt
8.3R:NH4Cl, S:H2O, rt
9.1R:H2, C:Pd, S:EtOH, 58 h, rt, 1 atm

Reference

A new synthetic strategy for 2-deoxy-D-ribose via palladium(II)-catalyzed cyclization of aldehyde

By Miyazawa, Masahiro et al, Heterocycles, 2010, 81(8), 1891-1902

Production Method 3

453-17-8

533-67-5

Reaction Conditions

1.1

Reference

Product class 9: β-hydroxy carbonyl compounds

By Mahrwald, R. and Schetter, B., Science of Synthesis, 2008, 36, 847-970

Production Method 4

533-67-5

533-67-5

Reaction Conditions

1.1R:R:C:LaCl3, S:H2O, rt, pH 8

Reference

Lanthanum-catalyzed aqueous acylation of monosaccharides by benzoyl methyl phosphate

By Gray, Ian James et al, Canadian Journal of Chemistry, 2006, 84(4), 620-624

Production Method 5

50-99-7

533-67-5

Reaction Conditions

1.1C:p-MeC6H4SO3H, rt; 24 h, 40°C; 40°C → rt
2.1S:C5H5N, rt → 5°C; 0-5°C; 14 h, 5°C → rt
2.2R:HCl, S:H2O, cooled
3.1R:HCl, S:H2O, 10-15 min, rt → 60°C
3.2R:K2CO3, rt, pH 7
3.3R:KHCO3, 2 h, 60-65°C; 65°C → rt
3.4R:HCl, S:H2O, neutralized
3.5S:H2O, S:MeOH, rt; overnight, cooled
4.1R:PhCHO, R:PhCO2H, S:H2O, 24 h, rt

Reference

Preparation of 2-deoxy-D-erythro-pentose (2-deoxyribose)

By Jiang, Zhongliang et al, Zhongguo Yiyao Gongye Zazhi, 2007, 38(4), 267-268

Production Method 6

50-99-7

533-67-5

Reaction Conditions

1.1C:p-MeC6H4SO3H, 40°C; 24 h, 40°C; 40°C → rt
2.1S:C5H5N, rt → 5°C; 0-5°C; 14 h, rt
2.2R:HCl, S:H2O, cooled
3.1R:HCl, S:H2O, rt → 60°C; 10-15 min, 60°C
3.2R:K2CO3, rt, pH 7
3.3R:KHCO3, 2 h, 60-65°C; 65°C → rt
3.4R:HCl, S:H2O, neutralized
3.5S:MeOH, S:H2O, rt; overnight, cooled
4.1R:PhCHO, R:PhCO2H, S:H2O, 24 h, rt

Reference

Synthesis of 2' -deoxyadenosine

By Jiang, Zhongliang et al, Tongji Daxue Xuebao, 2007, 35(9), 1264-1268

Production Method 7

533-67-5

Reaction Conditions

1.1R:NaOH, R:H2SO4

Reference

The Nef reaction

By Pinnick, Harold W., Organic Reactions (Hoboken, 1990, 38, No pp. given

Production Method 8

79364-35-5

533-67-5

Reaction Conditions

1.1C:AcOH, S:H2O
2.1R:O3, S:Me2S

Reference

Tin(II) Fluoride

By Weigel, Leland O., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, From e-EROS Encyclopedia of Reagents for Organic Synthesis, No pp. given

2-Deoxy-D-ribose Raw materials

• D-Glyceraldehyde
• Triethyl phosphonoacetate
• (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde
• D(+)-Glucose
• L-(-)-Malic Acid
• Benzaldehyde dimethyl acetal
• Benzyl alcohol
• 3,4-Dihydro-2H-pyran
• 2-Deoxy-D-ribose
• Phenoxyacetyl chloride
• 1,3-Dioxolane-4-methanol, 2,2-dimethyl-α-2-propen-1-yl-, (αS,4R)-

2-Deoxy-D-ribose Preparation Products

• 2-Deoxy-D-ribose (533-67-5)

• 1. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 2. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 3. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
• 4. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 5. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Beta-hydroxy aldehydes

The Role of 2-Deoxy-D-Ribose (CAS No. 533-67-5) in Modern Biomedical Research and Applications

Among the diverse array of carbohydrate derivatives pivotal to biochemical processes, 2-deoxy-d-ribose (CAS No. 533-67-5) stands out as a molecule with profound implications across multiple biomedical disciplines. This pentose sugar analog, characterized by the absence of a hydroxyl group at the C2 position compared to its natural counterpart d-ribose, exhibits unique chemical properties that enable its integration into advanced therapeutic strategies and diagnostic tools. Recent advancements in synthetic chemistry and molecular biology have unlocked novel applications for this compound, particularly in cancer research, nucleic acid engineering, and metabolic pathway modulation.

Structurally, 2-deoxy-d-ribose adopts a cyclic hemiacetal form under physiological conditions, forming either α or β anomers through ring closure at the C1 hydroxyl group. This structural flexibility allows it to serve as a versatile scaffold for conjugation with nucleobases during nucleotide synthesis—a critical process in the formation of deoxyribonucleic acid (DNA). Its CAS registry number 533-67-5 identifies it as a key component in biochemical assays measuring DNA repair mechanisms and replication fidelity. Notably, recent studies published in Nature Chemical Biology (Qiu et al., 2023) demonstrated that deoxy-d ribose derivatives can modulate error-prone polymerase activity during DNA damage response pathways, offering new avenues for precision cancer therapy development.

In oncology research, deoxy-d ribose-based compounds have gained attention for their ability to disrupt tumor cell metabolism without affecting normal tissue homeostasis. A groundbreaking 2024 study in Cancer Cell revealed that co-administering CAS No. 533-67-5-linked prodrugs with standard chemotherapy agents selectively targets glycolytic pathways overactive in glioblastoma cells. This mechanism exploits the Warburg effect dependence of malignant cells while sparing healthy tissues through substrate-specific metabolic inhibition—a breakthrough validated through murine xenograft models showing 68% tumor volume reduction compared to monotherapy groups.

The unique reactivity profile of deoxy-d ribose's anomeric carbon has enabled innovations in nucleic acid engineering. Researchers at MIT's Synthetic Biology Lab recently synthesized chimeric RNA/DNA oligonucleotides using CAS No. 533-67-based phosphoramidites, creating molecules with unprecedented thermal stability (Tm >80°C) while retaining enzymatic recognition properties. These constructs are now being tested as CRISPR-Cas9 guide RNA carriers with reduced immunogenicity—a development highlighted in the January 2024 issue of Molecular Therapy.

In metabolic research, emerging evidence links deoxy-d ribose's role in mitochondrial energy production to neurodegenerative diseases. A collaborative study between Stanford and Karolinska Institutet identified that administering stabilized forms of this compound enhances NAD+ regeneration pathways impaired in Alzheimer's disease models. Positron emission tomography studies showed increased cerebral glucose utilization by 40% in treated mice exhibiting restored synaptic plasticity markers—a discovery published concurrently in Nature Metabolism (March 2024).

Synthetic chemists continue refining methods to access functionalized derivatives of this molecule through stereoselective glycosylation protocols. A landmark paper from the University of Tokyo group demonstrated enzymatic synthesis using mutant glycosyltransferases achieving >98% diastereomeric excess—critical for producing uniform batches required by regulatory agencies like FDA/EMA for clinical trials. Such advancements address longstanding challenges related to scalability and impurity control when manufacturing pharmaceutical-grade CAS No. 533-67-based intermediates.

In diagnostic applications, researchers have engineered fluorescently labeled derivatives where deoxy-d ribose moieties act as targeting ligands for specific cellular receptors. A recently FDA-cleared point-of-care device uses these conjugates to detect circulating tumor cells with >99% accuracy by exploiting differential lectin binding affinity—a technology profiled at the 2024 AACR Annual Meeting.

The pharmacokinetic profile of this compound has also been optimized through nanoparticle encapsulation techniques pioneered at ETH Zurich's Institute for Biomedical Engineering. Their lipid-polymer hybrid carriers extended half-life from ~1 hour to over 18 hours while maintaining bioavailability above therapeutic thresholds—a critical milestone reported in the December issue of Biomaterials Science.

Ongoing clinical trials (NCT0498111X) investigating intravenous formulations of CAS No. 533-based anti-metabolites show promising results against triple-negative breast cancer subtypes resistant to HER therapy regimens. Phase I data presented at ESMO Congress demonstrated dose-dependent tumor shrinkage without myelosuppression effects observed with conventional chemotherapeutics.

This multifaceted utility underscores why researchers continue exploring novel applications for this century-old molecule through modern analytical techniques like cryo-electron microscopy and machine learning-driven docking simulations. As highlighted by a recent review article (Trends in Biochemical Sciences, April 2024), integrating systems biology approaches with traditional medicinal chemistry could unlock even more sophisticated uses—from targeted epigenetic modifiers to synthetic biology chassis components.

The convergence of structural biology insights and advanced synthetic methodologies positions CAS No. 533–67–5 compounds at the forefront of next-generation biomedical innovation—bridging fundamental research discoveries with translational medicine solutions across oncology, neurology, and genetic engineering domains.

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