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

Base Information

• Chemical Name: (2R,3S,4S)-2,3,4,5-tetrahydroxypentanal
• CAS No.: 7261-25-8
• Molecular Formula: C5H10O5
• Molecular Weight: 150.131
• 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: 7261-25-8.mol

Synonyms:Arabinose;L Arabinose;L-Arabinose

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

Chemical Property:

• Boiling Point: 375.4±42.0 °C(Predicted)
• PKA: 12.16±0.70(Predicted)
• PSA: 0.00000
• Density: 1.681±0.06 g/cm3(Predicted)
• LogP: 0.00000
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

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

There total 174 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:

3-O-α-L-rhamnopyranosyl polygalacic acid {28-O-α-L-rhamnopyranosyl(1→3)-β-D-xylopyranosyl(1→4)-α-L-rhamnopyranosyl(1→2)-[α-L-arabinofuranosyl(1→ 2)]-β-D-fucopyranosyl} ester → D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + L-rhamnose (73-34-7) + L-arabinose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + polygalacic acid (22338-71-2)

Guidance literature:

With sulfuric acid; water; In 1,4-dioxane; for 1h; Reflux;

DOI:10.1007/s11418-016-0998-9

Reference yield:

(-)-lyoniresinol; 3α-O-β-D-xylopyranoside → beta-D-xylofuranoside (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7,37110-85-3) + (-)-(8S,8'S,7'S)-lyoniresinol (3737-93-7,14464-90-5,23212-64-8,73745-49-0,31768-94-2)

Guidance literature:

With hydrogenchloride;

DOI:10.1248/cpb.43.1937

Reference yield:

7-methylguanosine (20244-86-4) → 7-methylguanine (578-76-7) + D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7)

Guidance literature:

With Caenorhabditis elegans group III nucleoside hydrolase C₄₂A mutant; water; sodium chloride; calcium chloride; In aq. buffer; at 25 ℃; pH=7.5; Concentration; Reagent/catalyst; Catalytic behavior; Kinetics; Enzymatic reaction;

DOI:10.1002/pro.3141

upstream raw materials:

3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-oleanolic acid 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester

3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester

adenine xyloside

tetra-O-acetyl-D-xylofuranose

Downstream raw materials:

(3aS,5R,6S,6aR)-2-<2,3,3a,5,6,6a-Hexahydro-6-hydroxy-5-(hydroxymethyl)furo<2,3-d>oxazol-2-yliden>cyanessigsaeure-methylester

methyl β-D-xylofuranoside

methyl xylofuranoside

furfural

Refernces

Glycomimetic building blocks: A divergent synthesis of epimers of shikimic acid

10.1021/ol201252x

The research focuses on the divergent synthesis of (-)-4-epi-shikimic acid, a glycomimetic building block, which is crucial for mimicking carbohydrates and their interactions with C-type lectins (CLECs), proteins involved in physiological and pathological processes. The synthesis route involves a one-pot zinc-mediated reductive ring opening of arabinofuranose, followed by a Barbier reaction and culminating in a ring-closing metathesis. The researchers used D-arabinose as the starting material, converting it to furanose 9 through acid-catalyzed ring contraction, and then to iodosugar 6 using Mitsunobu conditions. The key experiments included optimizing conditions for the Barbier reaction and ring-closing metathesis, with the latter being particularly challenging due to the reactivity of 1,1-disubstituted acrylates. The analyses used to monitor the progress and confirm the structures of the synthesized compounds included NMR and mass spectrometry. The overall yield of the synthetic route was 32%, and the utility of (-)-4-epi-shikimic acid for generating fucose-like compounds was demonstrated through conjugate addition of a thiol, resulting in a product with high diastereoselectivity.

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