1,4-Anhydro-D-xylitol

Base Information

• Chemical Name: 1,4-Anhydro-D-xylitol
• CAS No.: 53448-53-6
• Molecular Formula: C5H10O4
• Molecular Weight: 134.132
• European Community (EC) Number: 258-560-9
• UNII: 5KQL0CX6R6,8XWR7NN42F
• DSSTox Substance ID: DTXSID70964160
• Nikkaji Number: J295.958E
• Wikidata: Q82946086
• RXCUI: 1307762
• Mol file: 53448-53-6.mol

Synonyms:(D)-isomer of 1,4-anhydroxylitol;1,4-anhydro-D-xylitol;1,4-anhydroxylitol

Chemical Property of 1,4-Anhydro-D-xylitol

Chemical Property:

• Vapor Pressure: 7.04E-06mmHg at 25°C
• Refractive Index: 1.50
• Boiling Point: 337.7°Cat760mmHg
• PKA: 13.72±0.60(Predicted)
• Flash Point: 158°C
• PSA: 69.92000
• Density: 1.453g/cm³
• LogP: -1.90070
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 134.05790880
• Heavy Atom Count: 9
• Complexity: 95

Purity/Quality:

97% ^*data from raw suppliers

1,4-Anhydro-D-xylitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(O1)CO)O)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@H](O1)CO)O)O
• Uses: Used in the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-D-xylitol.

Technology Process of 1,4-Anhydro-D-xylitol

There total 65 articles about 1,4-Anhydro-D-xylitol 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: 100.0%

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose (14233-62-6,81799-90-8) → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With hydrogen; palladium dihydroxide;

DOI:10.1080/07328319808004714

Reference yield: 98.0%

1,4-anhydro-2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol (162635-55-4) → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 2h;

DOI:10.1016/0008-6215(94)00190-1

Reference yield: 95.0%

(3S,4S)-2-(dihydroxymethyl)tetrahydrofuran-3,4-diol → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 24h;

DOI:10.1039/c9gc00448c

upstream raw materials:

methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside

Adonitol

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose

(2R,3R,4S)-3,4-Bis-trimethylsilanyloxy-2-trimethylsilanyloxymethyl-tetrahydro-furan

Downstream raw materials:

1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

(2S,3S,4S)-3,4-dihydroxytetrahydrofuran-2-carboxylic acid

tri-O-benzoyl-DL-1,4-anhydro-ribitol

O⁵-trityl-DL-1,4-anhydro-xylitol