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

Base Information

• Chemical Name: (2R,3S,4S)-2,3,4,5-tetrahydroxypentanal
• CAS No.: 5328-37-0
• Molecular Formula: C5H10O5
• Molecular Weight: 150.131
• Hs Code.: 2940 00 00
• European Community (EC) Number: 205-699-8,243-619-3
• UNII: B40ROO395Z
• DSSTox Substance ID: DTXSID9039733
• Nikkaji Number: J14.786I
• Wikidata: Q407373
• Metabolomics Workbench ID: 53244
• Mol file: 5328-37-0.mol

Synonyms:Arabinose;L Arabinose;L-Arabinose

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.92E-06mmHg at 25°C
• Melting Point: 155ºC
• Refractive Index: 104 ° (C=10, H2O)
• Boiling Point: 415.5ºC at 760mmHg
• PKA: 12.46±0.20(Predicted)
• Flash Point: 219.2ºC
• PSA: 97.99000
• Density: 1.508g/cm3
• LogP: -2.73970
• Storage Temp.: room temp
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: almost transparency
• 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:

99% ^*data from raw suppliers

L-Arabinose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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
• Recent ClinicalTrials: Open-label Safety Extension Study Assessing Safety and Tolerability of LAI in Patients Who Participated in Study INS-212
• Description: L-Arabinose is considered a rare sugar that can be found naturally within the structures of most fruits and vegetables. Due to its low caloric sweetening effects, arabinose is commonly used in nutritional supplements and prescription drugs. In addition to its sweetening effects, when reacted with amino acid blends, using the Maillard Reaction, arabinose is able to contribute to the production of savory and meaty flavors used within the food and flavor industry.L-Arabinose is commonly used in the Flavor Industry to produce meaty or cooked/roasted flavors.
• Uses: The L-arabinose operon, also known as the araBAD operon, has been the subject of much biomolecular research. The operon directs the catabolism of arabinose in E. coli, and it is dynamically activated in the presence of arabinose and the absence of glucose. In synthetic biology, arabinose is often used as a one-way or reversible switch for protein expression under the Pbad promoter in E. coli. This on-switch can be negated by the presence of glucose or reversed off by the addition of glucose in the culture medium which is a form of catabolite repression. L-Arabinose is an arabinose isomer widely found in nature, while D-arabinose is less common. L-Arabinose is a constituent of many biopolymers that make up plant cell walls. This monosaccharide is often used in cell culture media, serving as a bacterial carbon source, and can be used to distinguish between bacteria based on their fermentation abilities. L-Arabinose, in the absence of glucose, induces transcription of the ara operon in E. coli that encodes L-arabinose catabolizing enzymes. It does this by binding to the AraC protein and activating the PBAD promoter. The PBAD promoter is used in plasmid vectors as a switch for protein expression that can be turned on by L-arabinose or turned off by addition of glucose. L-Arabinose is used as a substrate to identify, differentiate and characterize pentose sugar isomerase(s). L-Arabinose is used in the bioproduction of L-ribose.

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

There total 638 articles about (2R,3S,4S)-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:

cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside] → cyanidin (13306-05-3) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + caffeic acid (331-39-5,501-16-6)

Guidance literature:

Acidic conditions;

DOI:10.3987/COM-10-12012

Reference yield:

trilliumoside I → D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6,478518-52-4)

Guidance literature:

With trifluoroacetic acid; In 1,4-dioxane; water; at 90 ℃; for 3h;

DOI:10.1016/j.phytochem.2019.112125

Reference yield:

(23S,24S)-24-[(O-β-D-xylopyranosyl)oxy]-3β,23-dihydroxyspirosta-5,25(27)-diene-1-O-β-D-apiofuranosyl-(13)-O-(4-O-acetyla-L-rhamnopyranosyl)-(12)-O-[β-D-xylopyranosyl-(13)]-α-L-arabinopyranoside → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6,478518-52-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 80 ℃; for 2h;

DOI:10.1080/14786419.2018.1544980

upstream raw materials:

pyridine

L-ribulose

methanol

nitromethane

Downstream raw materials:

(1R)-1-piperidino-1,5-anhydro-L-arabitol

methyl-xylofuranoside

formic acid

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

Refernces

A total synthesis of OSW-1

10.1021/jo7018812

The research focuses on the total synthesis of OSW-1, a natural saponin with significant antitumor activities, which was synthesized from (+)-dehydroisoandrosterone, L-arabinose, and D-xylose on a gram scale. The study aimed to develop a new, efficient, and practical method for synthesizing OSW-1, a promising lead compound for the development of novel antitumor drugs, due to its potent cytotoxicity against various malignant tumor cells. The synthesis was achieved in 10 linear steps with an overall yield of 6.4%, starting from (+)-dehydroisoandrosterone. The research concluded that the developed synthetic strategy was reliable, with simple workup procedures, enabling large-scale synthesis and providing a foundation for the preparation of various OSW-1 derivatives for further studies on structure-activity relationships and potential anticancer therapeutics. Key chemicals used in the process included propanenitrile, 3-methylbutylmagnesium bromide, NaOH, TBS chloride, ethylene glycol, and a variety of other reagents and solvents employed in the multi-step synthesis procedure.

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.