UDP-L-arabinose

Base Information

• Chemical Name: UDP-L-arabinose
• CAS No.: 15839-78-8
• Molecular Formula: C14H22 N2 O16 P2
• Molecular Weight: 536.28
• DSSTox Substance ID: DTXSID70349271
• Nikkaji Number: J1.270.526C
• Wikidata: Q27131090
• Metabolomics Workbench ID: 41984
• Mol file: 15839-78-8.mol

Synonyms:UDP-L-arabinose;15839-78-8;UDP-beta-L-arabinopyranose;[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] hydrogen phosphate;UDP-beta-L-arabinose;UDP-ALPHA-D-XYLOPYRANOSE;P1-b-L-arabinopyranosyl ester;UDP-beta-L-Arap;Mono-b-L-arabinopyranosyl ester;CHEBI:61455;DTXSID70349271;AC-33222;Uridine 51-b-(trihydrogen pyrophosphate);uridine 5'-diphospho-beta-L-arabinopyranose;Q27131090;[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] hydrogen phosphate;uridine 5'-[3-(beta-L-arabinopyranosyl) dihydrogen diphosphate];[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid

Chemical Property of UDP-L-arabinose

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 296.64000
• Density: 1.96g/cm³
• LogP: -3.74230
• XLogP3: -6.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 536.04445661
• Heavy Atom Count: 34
• Complexity: 916

Purity/Quality:

97% ^*data from raw suppliers

UDP-b-L-arabinopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O)O)O
• Uses: UDP-b-L-arabinopyranose is used in synthesis of Schaftoside and Isoschaftoside.

Technology Process of UDP-L-arabinose

There total 6 articles about UDP-L-arabinose 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:

→ UDP-β-L-Arap (15839-78-8,21401-20-7,30329-30-7,38-57-3,97905-92-5,7164-64-9)

Guidance literature:

mit Hilfe von UDP-arabinose-4-epimerase aus Saemlingen von Phaseolus aureus;

DOI:10.1073/pnas.42.6.333 DOI:10.1021/ja01549a089

Reference yield:

uridine 5'-diphosphate-tetrabutyl ammonium + (2R,3R,4S,5S)-2-Iodo-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran → UDP-β-L-Arap (15839-78-8,21401-20-7,30329-30-7,38-57-3,97905-92-5,7164-64-9) + UDP-L-Ara (110222-42-9,21401-20-7,30329-30-7,38-57-3,97905-92-5,7164-64-9)

Guidance literature:

uridine 5'-diphosphate-tetrabutyl ammonium; (2R,3R,4S,5S)-2-Iodo-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran; In dichloromethane; for 4h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; for 1h;

With alkaline phosphatase; at 20 ℃; for 16h; pH=8; Title compound not separated from byproducts;

DOI:10.1080/07328309808001892

Reference yield:

L-(+)-arabinose (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) → UDP-β-L-Arap (15839-78-8,21401-20-7,30329-30-7,38-57-3,97905-92-5,7164-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / pyridine / 1 h / 0 °C

2.1: iodotrimethylsilane / CH₂Cl₂ / 0.5 h / 20 °C

3.1: CH₂Cl₂ / 4 h

3.2: tetrabutylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1 h

3.3: alkaline phosphatase / various solvent(s) / 16 h / 20 °C / pH 8

With pyridine; trimethylsilyl iodide; In dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Substitution / 3.2: Hydrolysis / 3.3: Hydrolysis;

DOI:10.1080/07328309808001892

upstream raw materials:

O¹-Phosphono-β-L-arabinopyranose

L-(+)-arabinose

per-O-trimethylsilyl-L-arabinose