22900-10-3

Basic information

• Product Name: 2-Deoxy-β-D-ribopyranose
• Synonyms: 2-Deoxy-β-D-ribopyranose;(2R,4S,5R)-oxane-2,4,5-triol;2-deoxy-β-D-erythro-pentopyranose;(2R,4S,5R)-tetrahydro-2H-pyran-2,4,5-triol
• CAS NO: 22900-10-3
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.1305
• Mol File: 22900-10-3.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Deoxy-β-D-ribopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-β-D-ribopyranose(22900-10-3)
• EPA Substance Registry System: 2-Deoxy-β-D-ribopyranose(22900-10-3)

Safety Data

• Hazardous Substances Data: 22900-10-3(Hazardous Substances Data)

Upstream product

• 75-07-0 acetaldehyde 
• 56-82-6 Glyceraldehyde 
• 961-07-9 2'-Deoxyguanosine 
• 85819-69-8 8-methyl-2'-deoxyguanosine 
• 1032468-38-4 anilide of 2-deoxy-L-ribose 
• 817621-87-7 2-deoxy-4,5-O-isopropylidene-L-ribose ethylene acetal 
• 817622-79-0 1-O-methyl-2-deoxy-3,4-O-isopropylidene-L-glucopyranoside 
• 288069-41-0 (2S,4R,5S)-(-)-4-allyl-5-hydroxy-2-phenyl-1,3-dioxane 
• 432492-83-6 benzyl 3,4-O-isopropylidene-2-O-[N-phenylthioxocarbamoyl]-β-L-arabinopyranoside 
• 432492-84-7 benzyl 3,4-O-isopropylidene-2-O-[1-imidazolyl(thiocarbonyl)]-β-L-arabinopyranoside 
• 432492-82-5 benzyl 3,4-O-isopropylidene-2-O-[(methyl-thio)thiocarbonyl]-β-L-arabinopyranoside 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 136737-24-1 benzyl 3,4-O-isopropylidene-2-O-[phenoxythiocarbonyl]-β-L-arabinopyranoside 

Downstream Products

• 142453-38-1 β-2,3-dideoxy-3-(6-(3-methyl-2-buten-1-ylamino)purin-9-yl)-D-threo-pentopyranose 
• 142453-37-0 α-2,3-dideoxy-3-(6-(3-methyl-2-buten-1-ylamino)purin-9-yl)-D-threo-pentopyranose 
• 533-67-5 2-Deoxy-D-ribose 
• 51255-18-6 1-O-methyl-β-2-deoxy-D-erythro-pentofuranose 
• 6160-56-1 methyl 2-deoxy-α-D-erythro-pentopyranoside 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 17676-20-9 methyl 2-deoxy-β-D-erythro-pentopyranoside 
• 124290-99-9 (4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol 
• 130472-43-4 2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-D-ribofuranose 
• 39967-60-7 2'-Deoxypseudouridine 
• 664988-34-5 5-(2-deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-2-dibenzylamino-3-methylpyridine 
• 664988-35-6 5-(2-deoxy-3,5-di-O-acetyl-α-D-ribofuranosyl)-2-dibenzylamino-3-methylpyridine 
• 664988-33-4 5-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α/β-D-ribofuranosyl]-2-dibenzylamino-3-methylpyridine 
• 664988-39-0 1-(6-Dibenzylamino-pyridin-3-yl)-2-((6S,7R)-7-hydroxy-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilocan-6-yl)-ethanone 

Relevant articles and documents

The 18O Isotope Shift in 13C Nuclear Magnetic Resonance Spectroscopy. 14. Kinetics of Oxygen Exchange at the Anomeric Carbon of D-Ribose and D-2-Deoxyribose

The kinetics of the oxygen-exchange reaction at the anomeric carbon atoms of D-ribose and D-2-deoxyribose (2-deoxy-D-erythro-pentose) were compared using the 18O isotope induced shift in 13C NMR spectroscopy.Measurements were made at a number of temperature and pH values.The oxygen-exchange reaction for these sugars is strongly pH-dependent, displaying regions of acid, water, and base catalysis.At 25 deg C the oxygen-exchange rate of D-ribose was found to be approximately 20-fold greater than the rate for D-glucose between pH 2 and 9.In turn, the oxygen-exchange rate for D-2-deoxyribose was greater than the rate for D-ribose by approximately 5-fold above pH 4 and by greater than 10-fold below pH 4.The results are analyzed in terms of steric and inductive effects on the hydration kinetics of the open-chain forms and by comparison with the hydration reaction of simple aldehydes.The study also includes quantitative data, based upon 13C NMR line intensities, for the various anomeric forms that exist in solutions of these sugars at the different temperature and pH values used in the kinetic measurements reported here.In each case, the oxygen-exchange reactions of the anomers are slow relative to the rate of anomerization, so that the anomers appear to exchange oxygen at the same rate.

Improved and practical synthesis of 2-deoxy-l-ribose by hypophosphite-mediated deoxygenation

An improved and practical route for a large-scale synthesis of 2-deoxy-L-ribose starting from L-arabinose has been developed. This is the first reported synthesis of 2-deoxy-L-ribose in which deoxygenation has been mediated by hypophosphite reagents instead of by organotin reagents.

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

We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step. The Japan Institute of Heterocyclic Chemistry.