2-Deoxy-D-ribose

Base Information

• Chemical Name: 2-Deoxy-D-ribose
• CAS No.: 533-67-5
• Deprecated CAS: 14050-34-1,176915-68-7,452-51-7,7208-80-2,18546-36-6
• Molecular Formula: C5H10O4
• Molecular Weight: 134.132
• Hs Code.: 2933.59
• European Community (EC) Number: 217-028-6,208-573-0
• UNII: LSW4H01241
• DSSTox Substance ID: DTXSID701015730,DTXSID70883428
• Nikkaji Number: J6.332K
• Wikipedia: Deoxyribose
• Wikidata: Q27887395
• Mol file: 533-67-5.mol

Synonyms:2 Deoxyribose;2-Deoxyribose;Deoxyribose

Chemical Property of 2-Deoxy-D-ribose

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 89-90 °C(lit.)
• Refractive Index: -56 ° (C=1, H2O)
• Boiling Point: 379.684 °C at 760 mmHg
• PKA: 12.61(at 25℃)
• Flash Point: 197.601 °C
• PSA: 69.92000
• Density: 1.516 g/cm³
• LogP: -1.55310
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: soluble
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 134.05790880
• Heavy Atom Count: 9
• Complexity: 83

Purity/Quality:

98% ^*data from raw suppliers

2-Deoxy-D-ribose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C(C=O)C(C(CO)O)O
• Isomeric SMILES: C(C=O)[C@@H]([C@@H](CO)O)O
• Description: 2-deoxy-D-Ribose is a reducing sugar formed as a degradation product during metabolism of thymidine by thymidine phosphorylase. It increases levels of reactive oxygen species (ROS) in HL-60 human leukemia cells when used at a concentration of 15 mM. 2-deoxy-D-Ribose (10 μM) induces tubulogenesis and migration of bovine aortic endothelial (BAE) cells. Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model.
• Uses: 2-Deoxy-D-ribose is used as a precursor to deoxyribonucleic acid. It induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione. Further, it is used in the synthesis of optically active dipyrrolyl alkanols from pyrroles on the surface of montmorillonite KSF clay.

Technology Process of 2-Deoxy-D-ribose

There total 59 articles about 2-Deoxy-D-ribose 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: 95.0%

sodium 3-deoxy-D-mannonate (93857-40-0) → 2-Deoxy-D-ribose (533-67-5)

Guidance literature:

sodium 3-deoxy-D-mannonate; With hydrogenchloride; In water; pH=5;

With sodium hypochlorite; acetic acid; In water; at 40 - 45 ℃; for 2h; pH=5 - 6;

Reference yield: 93.0%

D-arabino-3-deoxy-hexonic acid (1518-59-8) + 3-deoxy-D-arabino-hexono-1,4-lactone (50480-80-3) → 2-Deoxy-D-ribose (533-67-5)

Guidance literature:

D-arabino-3-deoxy-hexonic acid; 3-deoxy-D-arabino-hexono-1,4-lactone; With sodium carbonate; In water; at 20 ℃; pH=8.8;

With sodium hypochlorite; In water; for 1 - 4h; pH=4.5 - 5.0;

With sodium sulfite; In water;

Reference yield: 90.0%

(S)-2-Amino-6-{3-[(E)-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-methyl-acryloyl]-ureido}-hexanoic acid (87616-31-7) → 2-Deoxy-D-ribose (533-67-5) + (2S)-amino-6-(1-thyminyl)hexanoic acid (76945-38-5)

Guidance literature:

With pH 10.5; In water; at 90 ℃;

DOI:10.1021/ja00361a056

upstream raw materials:

3-deoxy-D-glucose

D-glucose

3-O-methyl-D-glucose

O³-(toluene-4-sulfonyl)-D-glucose

Downstream raw materials:

(E)-(5S,6R)-5,6,7-Trihydroxy-hept-2-enoic acid benzyl ester

2-deoxy-α-D-erythro-pentofuranose

2-deoxy-β-D-erythro-pentopyranose

2-deoxy-α-D-erythro-pentopyranose

Refernces

• 1、 Hoffmann, Reinhard W.,Endesfelder, Andreas,Zeiss, Hans-J.. "Conversion of 2,3-O-isopropylidene-D-glyceraldehyde into 2-deoxy-D-erythro-pentose". . p. 320 - 325. Retrieved 1983.
• 2、 de Lederkremer,Sala. "". . p. 385. Retrieved 1975.
• 3、 -. "Method for preparing 2-deoxy-D-ribose". Paragraph 0050; 0051; 0052; 0053; 0054. . Retrieved 2016/12/12.
• 4、 Lallana, Enrique,Freire, Felix,Seco, Jose Manuel,Quinoa, Emilio,Riguera, Ricardo. "The 1H NMR method for the determination of the absolute configuration of 1,2,3-prim,sec,sec-triols". . p. 4449 - 4452. Retrieved 2007/10/03.