D-Xylono-1,4-lactone

Base Information

• Chemical Name: D-Xylono-1,4-lactone
• CAS No.: 15384-37-9
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID801315147
• Nikkaji Number: J967.575B
• Wikidata: Q27101884
• Metabolomics Workbench ID: 50483
• Mol file: 15384-37-9.mol

Synonyms:D-Xylono-1,4-lactone;15384-37-9;D-Xylonic acid-1,4-lactone;18423-66-0;(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one;(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one;D-Xylonic acid gamma-lactone;Xylonic acid-1,4-lactone;MFCD00076092;D-Xylonic acid,g-lactone;Xylonic acid, |A-lactone;SCHEMBL1673173;CHEBI:16392;CUOKHACJLGPRHD-FLRLBIABSA-;DTXSID801315147;AMY24691;AKOS006272131;HY-W145487;BS-27418;CS-0214421;D-Xylono-1,4-lactone, >=95.0% (GC);C02753;H10214;W-201381;W-201654;Q27101884

Chemical Property of D-Xylono-1,4-lactone

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 8.77E-07mmHg at 25°C
• Melting Point: 97 °C(Solv: ethanol, 70% (64-17-5))
• Refractive Index: 1.58
• Boiling Point: 364.3 °C at 760 mmHg
• PKA: 12.10±0.60(Predicted)
• Flash Point: 162.8 °C
• PSA: 86.99000
• Density: 1.667 g/cm³
• LogP: -2.37410
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

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

D-Xylono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(=O)O1)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@H](C(=O)O1)O)O)O
• Uses: D-Xylono-1,4-lactone is an O-glycoside that can be rearranged to form intermediates for zaragozic acids through the [1,2]-Wittig rearrangement. Zaragozic acids are important in the inhibition of S.cer visiae, and thus sterol synthesis. D-Xylono-1,4-lactone is an O-glycoside that can be rearranged to form intermediates for zaragozic acids through the [1,2]-Wittig rearrangement. Zaragozic acids are important in the inhibition of S.cervisiae, and thus sterol synthesis.

Technology Process of D-Xylono-1,4-lactone

There total 17 articles about D-Xylono-1,4-lactone 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:

calcium D-ribonate (5346-83-8,7546-24-9,18905-33-4,22373-09-7,56512-56-2,62102-50-5,72656-08-7,74440-84-9,76386-31-7,123249-13-8,123277-10-1,133480-82-7,133480-83-8) → (4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-dihydro-furan-2-one (2782-09-4,3327-63-7,5336-08-3,13280-76-7,15384-34-6,15384-37-9,17676-01-6,18423-66-0,51532-86-6,68035-75-6,104196-15-8,133908-85-7) + D-Ribono-1,4-lactone (5336-08-3)

Guidance literature:

With sulfuric acid; In water; Yield given;

DOI:10.1016/0008-6215(91)80010-K

Reference yield:

D-xylonic acid (488-30-2,526-91-0,526-92-1,608-53-7,642-98-8,4172-43-4,4172-44-5,13171-74-9,13752-83-5,17812-24-7,17828-56-7,20663-19-8,28223-40-7) → D-xylono-1,4-lactone (15384-37-9)

Guidance literature:

In water-d2; Kinetics; Acidic conditions;

DOI:10.1080/07328303.2011.567424

Reference yield:

Adonitol (488-81-3) → ribonolactone (2782-09-4,3327-63-7,5336-08-3,13280-76-7,15384-34-6,15384-37-9,17676-01-6,18423-66-0,51532-86-6,68035-75-6,104196-15-8,133908-85-7) + DL-arabinonic acid-4-lactone (2782-09-4,3327-63-7,5336-08-3,13280-76-7,15384-34-6,15384-37-9,17676-01-6,18423-66-0,51532-86-6,68035-75-6,104196-15-8,133908-85-7)

Guidance literature:

With 1-Phenylbut-1-en-3-one; rhodium hydrido (PEt₃)3 complex; In N,N-dimethyl-formamide; at 80 ℃; for 5h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1998-1705

upstream raw materials:

D-Xylose

D-xylofuranose

D-xylose

D-xylonic acid

Downstream raw materials:

(E)-but-2-enoic acid

5-methyl-dihydro-furan-2-one

(+/-)-Tri-O-acetylarabono-1,4-lactone

(2S,4aR,7R,7aR)-7-hydroxy-2-phenyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

Refernces

• 1、 Regier, Jeffery,Ghanty, Supriya,Bolshan, Yuri. "Stereoselective Palladium-Catalyzed Arylation of Exo-Glycals with Aryl Iodides". supporting information. p. 524 - 530. Retrieved 2022/01/12.
• 2、 Zhang, Hu,Liu, Peng-Fei,Chen, Qiong,Wu, Qiong-You,Seville, Anne,Gu, Yu-Cheng,Clough, John,Zhou, Shao-Lin,Yang, Guang-Fu. "Synthesis and absolute configuration assignment of albucidin: A late-stage reductive deiodination by visible light photocatalysis". supporting information. p. 3482 - 3485. Retrieved 2016/04/09.