D(+)-Xylose

Base Information

• Chemical Name: D(+)-Xylose
• CAS No.: 58-86-6
• Deprecated CAS: 133-56-2,141492-19-5,41247-05-6,141492-19-5
• Molecular Formula: C5H10O5
• Molecular Weight: 150.131
• Hs Code.: 29400090
• European Community (EC) Number: 200-400-7,255-277-2,247-395-8
• NSC Number: 760130
• UNII: A1TA934AKO
• DSSTox Substance ID: DTXSID0023745
• Nikkaji Number: J2.806A
• Wikidata: Q27077130
• Metabolomics Workbench ID: 50315
• ChEMBL ID: CHEMBL1236821
• Mol file: 58-86-6.mol

Synonyms:Xylose, D-(8CI);(+)-Xylose;D-(+)-Xylose;Wood sugar;

Chemical Property of D(+)-Xylose

Chemical Property:

• Appearance/Colour: White crystal powder
• Vapor Pressure: 1.22E-08mmHg at 25°C
• Melting Point: 154-158°C(lit.)
• Refractive Index: 20 ° (C=10, H2O)
• Boiling Point: 331oC
• PKA: pKa (18°): 12.14
• Flash Point: 219.2oC
• PSA: 90.15000
• Density: 1.525
• LogP: -2.58230
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: soluble
• 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%min ^*data from raw suppliers

D-Xylose ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• 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
• General Description: D(+)-Xylose, also known as wood sugar, is a naturally occurring pentose sugar that serves as a key starting material in synthetic chemistry for the production of various cyclitol derivatives, such as conduritols and inositols. Its utility lies in its ability to undergo stereocontrolled transformations, including ring-closing metathesis and organometallic additions, enabling the synthesis of multifunctional compounds with potential biological relevance. The sugar's stereochemistry plays a crucial role in directing the diastereoselectivity of these reactions, making it a valuable chiral building block in organic synthesis.

Technology Process of D(+)-Xylose

There total 789 articles about D(+)-Xylose 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-β-D-xylopyranosyl-(1→2)-β-D-galactopyranoside (142506-19-2) → D-xylose (58-86-6) + cyanidin (13306-05-3) + D-Galactose (59-23-4)

Guidance literature:

With hydrogenchloride; water; at 95 ℃; for 2h;

DOI:10.1016/j.phytochem.2008.03.014

Reference yield:

p-nitrophenyl β-D-xylopyranoside (2001-96-9) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-xylose (58-86-6)

Guidance literature:

With Aspergillus niger GS1 β-xylosidase; In aq. acetate buffer; at 60 ℃; pH=5; Kinetics; Enzymatic reaction;

DOI:10.1016/j.procbio.2013.05.003

Reference yield:

cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + D-xylose (58-86-6) + cyanidin (13306-05-3) + D-glucose (50-99-7) + malonic acid (141-82-2) + para-coumaric acid (7400-08-0,50940-26-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.1016/j.phytol.2013.10.004

upstream raw materials:

pyridine

xylulose

oxalic acid

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

methyl β-D-xylofuranoside

methyl α-D-xylofuranoside

2,7-anhydro-β-D-ido-Heptulopyranose

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

Refernces

Enantio- and diastereodivergent synthetic route to multifarious cyclitols from D-xylose via ring-closing metathesis

10.1055/s-2008-1067260

The research focuses on the enantio- and diastereodivergent synthetic route to various cyclitols, including derivatives of conduritol B, conduritol F, myo-inositol, and chiro-inositol, starting from D-xylose. The key experimental steps involve a ring-closing metathesis process and a diastereodivergent organometallic addition to a D-xylose-derived aldehyde. The study explores the stereochemical outcomes of vinylmetal additions to carbohydrate-derived aldehydes, utilizing different vinylmetal reagents, solvents, and chelating agents to control the stereoselectivity of the reaction. The reactants include D-xylose, vinylmagnesium bromide, vinyllithium, and various chelating salts, while analyses used to confirm the structures and stereochemistry of the synthesized compounds encompass NMR spectroscopy, optical rotation measurements, and high-resolution mass spectrometry. The research provides insights into the factors influencing the stereochemistry of organometallic addition reactions and offers a practical synthetic route to a diverse group of cyclitol derivatives with potential biological importance.