D-Xylofuranose tetraacetate

Base Information

• Chemical Name: D-Xylofuranose tetraacetate
• CAS No.: 42927-46-8
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• Mol file: 42927-46-8.mol

Synonyms:D-Xylofuranose tetraacetate

Chemical Property of D-Xylofuranose tetraacetate

Chemical Property:

• PSA: 114.43000
• LogP: -0.29910

Purity/Quality:

1,2,3,5-Tetra-O-acetyl-D-xylofuranose ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2,3,5-Tetra-O-acetyl-D-xylofuranose is a starting material used for the synthesis of nucleotides.

Technology Process of D-Xylofuranose tetraacetate

There total 46 articles about D-Xylofuranose tetraacetate 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%

acetic anhydride (108-24-7) + methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside (90244-44-3,110415-62-8) → 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9,43225-70-3)

Guidance literature:

With sulfuric acid; In acetic acid;

DOI:10.3987/COM-08-S(F)59

Reference yield:

D-xylose (6763-34-4) + acetic anhydride (108-24-7) → tetra-O-acetyl-D-xylofuranose (42927-46-8) + α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0) + tetra-O-acetyl-β-D-xylopyranose (4049-33-6)

Guidance literature:

With pyridine; at 25 ℃; for 12h; Reagent/catalyst; Overall yield = 100 %; Overall yield = 20.14 g; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2017.03.008

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) + acetic anhydride (108-24-7) → 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) + 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

With pyridine; at 0 ℃; Yield given. Yields of byproduct given;

upstream raw materials:

D-Xylose

acetic anhydride

D-xylose

L-(+)-arabinose

Downstream raw materials:

α/β-Phenyltri-O-acetyl-D-thioxylofuranoside

2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-6-O-(diphenylcarbamoyl)guanine

D-xylofuranose

O²,O³,O⁵-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose

Refernces

• 1、 Herde, Zachary D.,John, Prathap D.,Alvarez-Fonseca, Dania,Satyavolu, Jagannadh,Burns, Christopher T.. "Stereoselective acetylation of hemicellulosic C5-sugars". . p. 1 - 14. Retrieved 2017/03/21.
• 2、 Xie, Ning,Taylor, Carol M.. "Synthesis of a dimer of β-(1,4)-l-arabinosyl-(2 S,4 R)-4-hydroxyproline inspired by art v 1, the major allergen of mugwort". supporting information; experimental part. p. 4968 - 4971. Retrieved 2010/12/25.