(2R,3R,4R)-2,3,4,5-tetrahydroxypentanal

Base Information

• Chemical Name: (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal
• CAS No.: 50-69-1
• Deprecated CAS: 58-91-3,6915-40-8,93781-19-2,6915-40-8,93781-19-2
• Molecular Formula: C5H10O5
• Molecular Weight: 150.131
• Hs Code.: 2933.59
• UNII: 681HV46001
• DSSTox Substance ID: DTXSID6043917,DTXSID101019160
• Nikkaji Number: J60.867J
• Wikidata: Q27120759
• Metabolomics Workbench ID: 56757
• Mol file: 50-69-1.mol

Synonyms:D Ribose;D-Ribose;Ribose

Chemical Property of (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.6E-07mmHg at 25°C
• Melting Point: 95 °C
• Refractive Index: -21 ° (C=1, H2O)
• Boiling Point: 375.4 °C at 760 mmHg
• PKA: 12.46±0.20(Predicted)
• Flash Point: 180.8 °C
• PSA: 97.99000
• Density: 1.681 g/cm³
• LogP: -2.73970
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless to light yellow
• Water Solubility.: Soluble in water. Insoluble in ether.
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 150.05282342
• Heavy Atom Count: 10
• Complexity: 104

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-Ribose ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C=O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@H](C=O)O)O)O)O
• Identification and Nomenclature: It is identified as a D-ribose and an aldehydo-ribose, being the enantiomer of an aldehydo-L-ribose. Its systematic name is (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal.
• Occurrence: Found naturally in organisms such as Streptomyces sporangiiformans and Arabidopsis thaliana.
• Versatility: Known by various names including ribose, aldehydo-d-ribo-pentose, and ribo-2,3,4,5-tetrahydroxyvaleraldehyde. Its unique structure and properties make it useful in pharmaceuticals, biochemistry, and organic synthesis.
• Precursor to D-Ribose: Serves as a precursor to D-ribose, which is a crucial component of ribonucleic acid (RNA) and certain coenzymes.
• Cyclic Forms: Like most sugars, ribose exists as a mixture of cyclic forms in equilibrium with its linear form, and these readily interconvert especially in aqueous solution. In its linear form, ribose can be recognised as the pentose sugar with all of its hydroxyl functional groups on the same side in its Fischer projection. d-Ribose has these hydroxyl groups on the right hand side and is associated with the systematic name (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal, whilst l-ribose has its hydroxyl groups appear on the left hand side in a Fischer projection.

Technology Process of (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal

There total 136 articles about (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal 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:

Glycolaldehyde (141-46-8) + Glyceraldehyde (56-82-6,367-47-5,26793-98-6) → DL-dendroketose (470-14-4) + arabinose (20235-19-2) + (+/-)-xylose (41247-05-6) + rac-Ribose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + rac-lyxose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + Dendroaldose (4072-92-8,4096-61-1,4211-40-9,4573-78-8,5612-45-3,6747-98-4,90409-92-0)

Guidance literature:

With calcium hydroxide; at 23 ℃; Mechanism; Kinetics;

Reference yield:

Glycolaldehyde (141-46-8) + Glyceraldehyde (56-82-6,367-47-5,26793-98-6) → DL-dendroketose (470-14-4) + arabinose (20235-19-2) + (+/-)-xylose (41247-05-6) + rac-Ribose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + rac-lyxose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + Dendroaldose (4072-92-8,4096-61-1,4211-40-9,4573-78-8,5612-45-3,6747-98-4,90409-92-0)

Guidance literature:

With calcium hydroxide; at 23 ℃; Mechanism; Kinetics;

Reference yield:

dihydroxyacetone (96-26-4,26776-70-5) + Glycolaldehyde (141-46-8) → DL-dendroketose (470-14-4) + arabinose (20235-19-2) + (+/-)-xylose (41247-05-6) + rac-Ribose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + rac-lyxose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) + DL-erythro-[2]pentulose (488-84-6,527-50-4,551-84-8,2042-27-5,5556-48-9,5962-29-8,7558-89-6,25577-44-0,83946-43-4)

Guidance literature:

With calcium hydroxide; at 23 ℃; Mechanism; Kinetics;

upstream raw materials:

pyridine

D-ribulose

xylulose

nitromethane

Downstream raw materials:

D-ribulose

1,2,3,5-tetraacetylribose

tetra-O-acetyl-D-ribofuranose

1,2,3,4-tri-O-acetyl-α-D-ribopyranose

Refernces

Synthesis and anti-HBV activity of isocytosine derivatives linked to 5-position of methyl β-p-ribofuranoside

10.3184/030823407X225473

The research presents the synthesis and anti-hepatitis B virus (HBV) activity of isocytosine derivatives linked to the 5-position of methyl β-D-ribofuranoside. The study involves the synthesis of a series of isocytosine derivatives through a multi-step process, utilizing reactants such as d-ribose, tosylation reagents, potassium phthalimide, and various 2-methyl-thiouracils. The synthesized compounds were evaluated for in vitro cytotoxicity against HBV, with some showing moderate activity. The experiments included nucleophilic substitution reactions, deprotection steps using acids like 70% AcOH, and purification through chromatographic techniques. The structures and purities of the synthesized compounds were confirmed using techniques like 1H NMR spectroscopy, EI-MS, and elemental analysis. The anti-HBV activity was screened using the Hep G2 2.2.15 cell method, revealing selective indexes for the compounds that indicated their potential as antiviral agents.

Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerization

10.1021/ol0483495

The study investigates the synthesis of seven-membered ring glycals through endo-selective alkynol cycloisomerization catalyzed by tungsten carbonyl. The researchers used alkynyldiols as substrates, which undergo cycloisomerization to form the corresponding seven-membered cyclic enol ethers with good yields and virtually complete regioselectivity favoring endo-mode cyclization. The study began with the conversion of D-ribose into alkynyl alcohol precursors, which were then used to produce alkynyldiols. The unexpected regioselectivity for seven-membered ring formation is likely due to the presence of the dioxolane structure tethering the terminal alkyne and diol functional groups. The study demonstrated that this transformation is general for various diastereomers of acetonide-protected alkynyldiols derived from different sugars, including D-lyxose, D-xylose, and L-arabinose. The availability of these septanose glycals could significantly advance the synthesis of structurally unusual hexoseptanose glycosides.

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