1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose

Base Information

• Chemical Name: 1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose
• CAS No.: 4049-33-6
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• Hs Code.: 2940000080
• European Community (EC) Number: 692-834-2
• Nikkaji Number: J615.805F
• Wikidata: Q76149070
• ChEMBL ID: CHEMBL513262
• Mol file: 4049-33-6.mol

Synonyms:4049-33-6;1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose;(2S,3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;1,2,3,4-Tetra-O-acetyl-b-D-xylopyranose;[(3R,4S,5R,6S)-4,5,6-triacetyloxyoxan-3-yl] acetate;.beta.-D-Xylopyranose, tetraacetate;Xylopyranose, tetraacetate, .beta.-D-;b-D-Xylopyranose, tetraacetate;tetraacetate;Tetra-O-acetyl-.beta.-D-xylopyranose;1,2,3,4-Tetra-O-acetylpentopyranose #;beta-xylose tetraacetate;Maybridge1_004120;CHEMBL513262;SCHEMBL3570498;beta-D-Xylopyranose tetraacetate;HMS553D08;MFCD00069790;CCG-239738;1,2,3,4-tetra-O-acetyl beta-D-xylose;AS-18984;1,2,3,4-Tetra-O-acetyl--D-xylopyranose;CS-0098203;1,2,3,4-Tetra-O-acetyl-..-D-xylopyranose;1,2,3,4-Tetra-O-acetyl-|A-D-xylopyranose;F20520;1,2,3,4-Tetra-O-acetyl-.beta.-D-xylopyranose;A825133;Acetyl 2,3,4-tri-O-acetyl-.beta.-D-xylopyranoside;W-202664;(2S,3R,4S,5R)-3,4,5-TRIS(ACETYLOXY)OXAN-2-YL ACETATE

Chemical Property of 1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose

Chemical Property:

• Vapor Pressure: 1.87E-05mmHg at 25°C
• Melting Point: 123-125 °C
• Refractive Index: 1.475
• Boiling Point: 362.9 °C at 760 mmHg
• Flash Point: 157 °C
• PSA: 114.43000
• Density: 1.29 g/cm³
• LogP: -0.29910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 318.09508215
• Heavy Atom Count: 22
• Complexity: 458

Purity/Quality:

98%, ^*data from raw suppliers

1,2,3,4-Tetra-O-acetyl-b-D-xylopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose

There total 80 articles about 1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose 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%

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) → 1,2,3,4-tetra-O-acetyl-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2003.12.034

Reference yield: 100.0%

D-xylose (6763-34-4) + acetic anhydride (108-24-7) → 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)

Guidance literature:

D-xylose; With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 0.166667h; Inert atmosphere;

acetic anhydride; In dichloromethane; at 0 - 25 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2017.03.008

Reference yield: 94.0%

D-Xylose (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) → 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)

Guidance literature:

With dmap; In pyridine; Inert atmosphere;

DOI:10.1016/j.tet.2014.07.052

upstream raw materials:

D-xylose

acetic anhydride

D-Xylose

acetyl chloride

Downstream raw materials:

(4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside)

(4-nitro-phenyl)-(tri-O-acetyl-α-L-arabinopyranoside)

2-methylphenyl-α-L-arabinopyranoside

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

Refernces

• 1、 Feast, George C.,Lepitre, Thomas,Mulet, Xavier,Conn, Charlotte E.,Hutt, Oliver E.,Savage, G. Paul,Drummond, Calum J.. "The search for new amphiphiles: Synthesis of a modular, high-throughput library". . p. 1578 - 1588. Retrieved 2014.
• 2、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 3、 Movahhed, Sohajl,Westphal, Julia,Kempa, Alexander,Schumacher, Christian Eric,Sperlich, Julia,Neud?rfl, J?rg-Martin,Teusch, Nicole,Hochgürtel, Matthias,Schmalz, Hans-Günther. "Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation". supporting information. p. 11574 - 11579. Retrieved 2021/07/02.