113890-34-9

Basic information

• Product Name: 2-Deoxy-alpha-L-erythro-pentopyranose
• Synonyms: 2-DEOXY-ALPHA-L-ERYTHRO-PENTOPYRANOSE;A-L-ERYTHRO-PENTOPYRANOSE,2-DEOXY-;2-Deoxy-a-L-erythro pentopyranose;2-Deoxy-α-L-erythro-pentopyranose
• CAS NO: 113890-34-9
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• Mol File: 113890-34-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 332.055 °C at 760 mmHg
• Flash Point: 154.621 °C
• Appearance: /
• Density: 1.516 g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.579
• PKA: 12.78±0.60(Predicted)
• CAS DataBase Reference: 2-Deoxy-alpha-L-erythro-pentopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-alpha-L-erythro-pentopyranose(113890-34-9)
• EPA Substance Registry System: 2-Deoxy-alpha-L-erythro-pentopyranose(113890-34-9)

Safety Data

• Hazardous Substances Data: 113890-34-9(Hazardous Substances Data)

Usage

General Description

2-Deoxy-alpha-L-erythro-pentopyranose, also known as 2-deoxyribose, is a five-carbon sugar derived from ribose. It is a key component of DNA, where it forms the backbone of the double helix structure. The 2-deoxyribose molecule is made up of a pentose sugar ring with a hydroxyl group missing at the 2' position, which distinguishes it from ribose. This chemical is essential for the formation of nucleotides, the building blocks of DNA, and plays a crucial role in the storage and transmission of genetic information. Additionally, 2-deoxyribose is used in various biochemical and medical research applications, including the synthesis of nucleosides and nucleotides for pharmaceutical purposes.

InChI:InChI=1/C5H10O4/c6-3-1-5(8)9-2-4(3)7/h3-8H,1-2H2/t3-,4+,5-/m1/s1

Upstream product

• 817621-81-1 (3S,4R)-6-methoxytetrahydro-2H-pyran-3,4-diol 
• 1032468-38-4 anilide of 2-deoxy-L-ribose 
• 64429-68-1 methyl 3,4-O-isopropylidene-2-deoxy-β-L-arabinopyranoside 
• 6960-39-0 methyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 91-09-8 methyl β-L-arabinopyranoside 
• 1373340-79-4 methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-β-L-arabinopyranoside 
• 1032153-57-3 1-t-butyl-2-deoxy-L-ribopyranose 
• 152202-52-3 L-arabinal 
• 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 

Downstream Products

• 863396-35-4 methyl-2-deoxyribopyranoside 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 112230-88-3 (E)-4-((4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 130144-85-3 (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran 
• 130144-86-4 (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran 
• 602301-70-2 (E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate 
• 171030-11-8 15-epi-lipoxin A4 
• 441352-22-3 (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-oxepan-3-one 
• 250226-68-7 (2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-oxepan-3-ol 
• 441352-42-7 (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one 
• 250226-81-4 [(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-2-((6S,7R)-6-benzyloxy-7-benzyloxymethyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 441352-37-0 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester 
• 351186-83-9 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-5a-methoxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol 

Relevant articles and documents

2-Deoxy-L-ribose from an L-arabinono-1,5-lactone

A practical synthesis of 2-deoxy-L-ribose from L-arabinose depends on the efficient reduction by iodide of a triflate α to a lactone. The X-ray crystal structure of 3,4-O-isopropylidene-L-arabinono-1,5-lactone is reported.

2-deoxy-L-ribose preparation method

The invention relates to a method for preparing 2-deoxidation-L-ribose based on L-arabinose as a raw material. The method comprises following seven steps: protection, group activation, transformation, deprotection and purification. Synthesis reaction cond

Stability of N-glycosidic bond of (5′ S)-8,5′-Cyclo-2′- deoxyguanosine

8,5′-Cyclopurine deoxynucleosides are unique tandem lesions containing an additional covalent bond between the base and the sugar. These mutagenic and genotoxic lesions are repaired only by nucleotide excision repair. The N-glycosidic (or C1′-N9) bond of 2′-deoxyguanosine (dG) derivatives is usually susceptible to acid hydrolysis, but even after cleavage of this bond of the cyclopurine lesions, the base would remain attached to the sugar. Here, the stability of the N-glycosidic bond and the products formed by formic acid hydrolysis of (5′S)-8,5′-cyclo-2′-deoxyguanosine (S-cdG) were investigated. For comparison, the stability of the N-glycosidic bond of 8,5′-cyclo-2′,5′-dideoxyguanosine (ddcdG), 8-methyl-2′-deoxyguanosine (8-Me-dG), 7,8-dihydro-8-oxo-2′- deoxyguanosine (8-Oxo-dG), and dG was also studied. In various acid conditions, S-cdG and ddcdG exhibited similar stability to hydrolysis. Likewise, 8-Me-dG and dG showed comparable stability, but the half-lives of the cyclic dG lesions were at least 5-fold higher than those of dG or 8-Me-dG. NMR studies were carried out to investigate the products formed after the cleavage of the C1′-N9 bond. 2-Deoxyribose generated α and β anomers of deoxyribopyranose and deoxyribopyranose oligomers following acid treatment. S-cdG gave α- and β-deoxyribopyranose linked guanine as the major products, but α and β anomers of deoxyribofuranose linked guanine and other products were also detected. The N-glycosidic bond of 8-Oxo-dG was found exceptionally stable in acid. Computational studies determined that both the protonation of the N7 atom and the rate constant in the bond breaking step control the overall kinetics of hydrolysis, but both varied for the molecules studied indicating a delicate balance between the two steps. Nevertheless, the computational approach successfully predicted the trend observed experimentally. For 8-Oxo-dG, the low pKa of O8 and N3 prevented appreciable protonation, making the free energy for N-glycosidic bond cleavage in the subsequent step very high.

PREPARATION METHOD OF 2-DEOXY-L-RIBOSE

A method of preparing 2-deoxy-L-ribose represented by the following formula I is disclosed. The preparation method includes the steps of: treating L-arabinose with an alcohol solvent in the presence of an acid to prepare 1-alkoxy-L-arabinopyranose; allowi